Article: Organocatalytic asymmetric tandem Michael-Henry reactions: a highly stereoselective synthesis of multifunctionalized cyclohexanes with two quaternary stereocenters.
Organic letters
2008 Volume 10, Issue 12, Page(s) 2437–2440
Abstract: A novel organocatalytic asymmetric tandem Michael-Henry reaction catalyzed by 9-amino-9 ... asymmetric Henry reaction of common ketones as acceptors is shown. ...
Abstract | A novel organocatalytic asymmetric tandem Michael-Henry reaction catalyzed by 9-amino-9-deoxyepiquinine (VI) has been developed. The reaction was efficiently catalyzed by catalyst VI to give highly functionalized cyclohexanes with four stereogenic carbons including two quaternary stereocenters in excellent enantioselectivities (97 to >99% ee) and high diastereoselectivities (93:7-99:1 dr). Thus, the first organocatalytic asymmetric Henry reaction of common ketones as acceptors is shown. |
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MeSH term(s) | Catalysis ; Cyclohexanes/chemical synthesis ; Cyclohexanes/chemistry ; Ketones/chemistry ; Models, Molecular ; Molecular Structure ; Quinolizines/chemistry ; Stereoisomerism |
Chemical Substances | 9-amino-9-deoxyepiquinine ; Cyclohexanes ; Ketones ; Quinolizines |
Language | English |
Publishing date | 2008-06-19 |
Publishing country | United States |
Document type | Journal Article ; Research Support, Non-U.S. Gov't |
ISSN | 1523-7060 |
ISSN | 1523-7060 |
DOI | 10.1021/ol8007183 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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