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  1. Article: Solvent-Free Methallylboration of Ketones Accelerated by tert-Alcohols

    Zhang, Yongda / Li Ning / Goyal Navneet / Li Guisheng / Lee Heewon / Lu Bruce Z / Senanayake Chris H

    Journal of organic chemistry. 2013 June 07, v. 78, no. 11

    2013  

    Abstract: A solvent- and metal-free process has been developed for the direct methallylboration of ketones employing the stable B-methallylborinane 1, which was accelerated by tertiary alcohols. In the presence of 2.0 equiv of readily available tertiary alcohols ... ...

    Abstract A solvent- and metal-free process has been developed for the direct methallylboration of ketones employing the stable B-methallylborinane 1, which was accelerated by tertiary alcohols. In the presence of 2.0 equiv of readily available tertiary alcohols such as tert-amyl alcohol, the methallylation products were prepared at room temperature in excellent yields. The salient features of the described process include simple operation, high efficiency, and mild reaction conditions.
    Keywords alcohols ; ambient temperature ; chemical reactions ; chemical structure ; ketones ; organic chemistry
    Language English
    Dates of publication 2013-0607
    Size p. 5775-5781.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo4006574
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  2. Article ; Online: Synthesis of 8-arylquinolines via one-pot Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling.

    Zhang, Yongda / Gao, Joe / Li, Wenjie / Lee, Heewon / Lu, Bruce Z / Senanayake, Chris H

    The Journal of organic chemistry

    2011  Volume 76, Issue 15, Page(s) 6394–6400

    Abstract: A one-pot process has been developed for the synthesis of 8-arylquinolines via Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling with aryl halides using n-BuPAd(2) as ligand. Yields of up to 98% were obtained. ...

    Abstract A one-pot process has been developed for the synthesis of 8-arylquinolines via Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling with aryl halides using n-BuPAd(2) as ligand. Yields of up to 98% were obtained.
    MeSH term(s) Catalysis ; Hydrocarbons, Halogenated/chemistry ; Ligands ; Molecular Structure ; Palladium/chemistry ; Quinolines/chemical synthesis ; Quinolines/chemistry
    Chemical Substances Hydrocarbons, Halogenated ; Ligands ; Quinolines ; Palladium (5TWQ1V240M)
    Language English
    Publishing date 2011-08-05
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo200904g
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  3. Article ; Online: One-pot and regiospecific synthesis of 2,3-disubstituted indoles from 2-bromoanilides via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.

    Lu, Bruce Z / Wei, Han-Xun / Zhang, Yongda / Zhao, Wenyi / Dufour, Marine / Li, Guisheng / Farina, Vittorio / Senanayake, Chris H

    The Journal of organic chemistry

    2013  Volume 78, Issue 9, Page(s) 4558–4562

    Abstract: A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination. ...

    Abstract A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.
    MeSH term(s) Amides/chemistry ; Anilides/chemistry ; Catalysis ; Cyclization ; Hydrocarbons, Brominated/chemistry ; Indoles/chemical synthesis ; Indoles/chemistry ; Molecular Structure ; Organometallic Compounds/chemistry ; Oxidation-Reduction ; Palladium/chemistry
    Chemical Substances Amides ; Anilides ; Hydrocarbons, Brominated ; Indoles ; Organometallic Compounds ; Palladium (5TWQ1V240M)
    Language English
    Publishing date 2013-05-03
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo302679f
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Solvent-free methallylboration of ketones accelerated by tert-alcohols.

    Zhang, Yongda / Li, Ning / Goyal, Navneet / Li, Guisheng / Lee, Heewon / Lu, Bruce Z / Senanayake, Chris H

    The Journal of organic chemistry

    2013  Volume 78, Issue 11, Page(s) 5775–5781

    Abstract: A solvent- and metal-free process has been developed for the direct methallylboration of ketones employing the stable B-methallylborinane 1, which was accelerated by tertiary alcohols. In the presence of 2.0 equiv of readily available tertiary alcohols ... ...

    Abstract A solvent- and metal-free process has been developed for the direct methallylboration of ketones employing the stable B-methallylborinane 1, which was accelerated by tertiary alcohols. In the presence of 2.0 equiv of readily available tertiary alcohols such as tert-amyl alcohol, the methallylation products were prepared at room temperature in excellent yields. The salient features of the described process include simple operation, high efficiency, and mild reaction conditions.
    MeSH term(s) Alcohols/chemical synthesis ; Alcohols/chemistry ; Boranes/chemistry ; Ketones/chemistry ; Molecular Structure
    Chemical Substances Alcohols ; Boranes ; Ketones
    Language English
    Publishing date 2013-06-07
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo4006574
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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  5. Article: One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination

    Lu, Bruce Z / Wei Han-Xun / Zhang Yongda / Zhao Wenyi / Dufour Marine / Li Guisheng / Farina Vittorio / Senanayake Chris H

    Journal of organic chemistry. 2013 May 03, v. 78, no. 9

    2013  

    Abstract: A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination. ...

    Abstract A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.
    Keywords catalytic activity ; chemical reactions ; chemical structure ; indoles ; organic chemistry ; palladium ; regioselectivity
    Language English
    Dates of publication 2013-0503
    Size p. 4558-4562.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo302679f
    Database NAL-Catalogue (AGRICOLA)

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  6. Article: Asymmetric Synthesis of Sulfinamides Using (−)-Quinine as Chiral Auxiliary

    Zhang, Yongda / Chitale Sampada / Goyal Navneet / Grinberg Nelu / Han Zhengxu S / Lee Heewon / Li Guisheng / Lu Bruce Z / Ma Shengli / Senanayake Chris H / Shen Sherry

    Journal of organic chemistry. 2012 Jan. 06, v. 77, no. 1

    2012  

    Abstract: A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent ... ...

    Abstract A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.
    Keywords chemical reactions ; chemical structure ; enantioselectivity ; organic chemistry ; quinine
    Language English
    Dates of publication 2012-0106
    Size p. 690-695.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo201825b
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  7. Article ; Online: An Enantioselective Synthesis of an 11-β-HSD-1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)-3,3'-F2-BINOL.

    Zhang, Yongda / Wu, Jiang-Ping / Li, Guisheng / Fandrick, Keith R / Gao, Joe / Tan, Zhulin / Johnson, Joe / Li, Wenjie / Sanyal, Sanjit / Wang, Jun / Sun, Xiufeng / Lorenz, Jon C / Rodriguez, Sonia / Reeves, Jonathan T / Grinberg, Nelu / Lee, Heewon / Yee, Nathan / Lu, Bruce Z / Senanayake, Chris H

    The Journal of organic chemistry

    2016  Volume 81, Issue 6, Page(s) 2665–2669

    Abstract: An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric ... ...

    Abstract An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric methallylation of 3-chloro-1-phenylpropan-1-one catalyzed by the highly effective organocatalyst (S)-3,3'-F2-BINOL under solvent-free and metal-free conditions.
    MeSH term(s) 11-beta-Hydroxysteroid Dehydrogenases/antagonists & inhibitors ; 11-beta-Hydroxysteroid Dehydrogenases/chemistry ; Catalysis ; Ketones/chemistry ; Naphthols/chemical synthesis ; Naphthols/chemistry ; Propane/analogs & derivatives ; Propane/chemical synthesis ; Propane/chemistry ; Stereoisomerism
    Chemical Substances 3,3'-F2-BINOL ; 3-chloro-1-phenylpropan-1-one ; Ketones ; Naphthols ; 11-beta-Hydroxysteroid Dehydrogenases (EC 1.1.1.146) ; Propane (T75W9911L6)
    Language English
    Publishing date 2016-03-18
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.6b00189
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: A practical mild, one-pot, regiospecific synthesis of 2,3-disubstituted indoles via consecutive Sonogashira and Cacchi reactions.

    Lu, Bruce Z / Zhao, Wenyi / Wei, Han-Xun / Dufour, Marine / Farina, Vittorio / Senanayake, Chris H

    Organic letters

    2006  Volume 8, Issue 15, Page(s) 3271–3274

    Abstract: Structure: see text] A practical one-pot, regiospecific three-component process for the synthesis of 2,3-disubstituted indoles was developed via consecutive Pd-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination. ...

    Abstract [Structure: see text] A practical one-pot, regiospecific three-component process for the synthesis of 2,3-disubstituted indoles was developed via consecutive Pd-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.
    MeSH term(s) Catalysis ; Combinatorial Chemistry Techniques ; Indoles/chemical synthesis ; Molecular Structure ; Palladium/chemistry
    Chemical Substances Indoles ; Palladium (5TWQ1V240M)
    Language English
    Publishing date 2006-07-20
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7060
    ISSN 1523-7060
    DOI 10.1021/ol061136q
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  9. Article: An Enantioselective Synthesis of an 11-β-HSD-1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)-3,3′-F2-BINOL

    Zhang, Yongda / Fandrick Keith R / Gao Joe / Grinberg Nelu / Johnson Joe / Lee Heewon / Li Guisheng / Li Wenjie / Lorenz Jon C / Lu Bruce Z / Reeves Jonathan T / Rodriguez Sonia / Sanyal Sanjit / Senanayake Chris H / Sun Xiufeng / Tan Zhulin / Wang Jun / Wu Jiang-Ping / Yee Nathan

    Journal of organic chemistry. 2016 Mar. 18, v. 81, no. 6

    2016  

    Abstract: An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric ... ...

    Abstract An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric methallylation of 3-chloro-1-phenylpropan-1-one catalyzed by the highly effective organocatalyst (S)-3,3′-F₂-BINOL under solvent-free and metal-free conditions.
    Keywords catalytic activity ; chemical reactions ; chemical structure ; enantioselective synthesis ; organic chemistry ; organic compounds
    Language English
    Dates of publication 2016-0318
    Size p. 2665-2669.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Facs.joc.6b00189
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  10. Article: Control of diastereoselectivity by solvent effects in the addition of Grignard reagents to enantiopure t-butylsulfinimine: syntheses of the stereoisomers of the hydroxyl derivatives of sibutramine.

    Lu, Bruce Z / Senanayake, Chris / Li, Nansheng / Han, Zhengxu / Bakale, Roger P / Wald, Stephen A

    Organic letters

    2005  Volume 7, Issue 13, Page(s) 2599–2602

    Abstract: reaction: see text] An efficient method has been developed to prepare all four isomers of the hydroxyl derivatives of sibutramine by addition of Grignard reagents (R)- or (S)-5 to a single enantiomer of sulfinyl imine (R)-1 simply by tuning the reaction ...

    Abstract [reaction: see text] An efficient method has been developed to prepare all four isomers of the hydroxyl derivatives of sibutramine by addition of Grignard reagents (R)- or (S)-5 to a single enantiomer of sulfinyl imine (R)-1 simply by tuning the reaction solvent. The phenomenon of the reversed diastereoselectivity in CH(2)Cl(2) and THF implied that the reaction may proceed through a chelated cyclic transition state in CH(2)Cl(2) and nonchelated acyclic transition state in THF.
    MeSH term(s) Cyclobutanes/chemical synthesis ; Cyclobutanes/chemistry ; Hydroxyl Radical/chemistry ; Indicators and Reagents ; Molecular Structure ; Solvents ; Stereoisomerism ; Sulfinic Acids/chemistry
    Chemical Substances Cyclobutanes ; Indicators and Reagents ; Solvents ; Sulfinic Acids ; Hydroxyl Radical (3352-57-6) ; sibutramine (WV5EC51866)
    Language English
    Publishing date 2005-06-23
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7060
    ISSN 1523-7060
    DOI 10.1021/ol0507017
    Database MEDical Literature Analysis and Retrieval System OnLINE

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