Article ; Online: Tandem 6pi-electrocyclization and cycloaddition of nitrodienes to yield multicyclic nitroso acetals.
Journal of the American Chemical Society
2010 Volume 132, Issue 26, Page(s) 8876–8877
Abstract: Upon heating, nitrodienes rearrange through 6pi-electrocyclization to form nitronate intermediates, which can be captured through tandem [3 + 2] dipolar cycloadditions to form highly functionalized nitroso acetals. The one-pot, two-step domino process is ...
Abstract | Upon heating, nitrodienes rearrange through 6pi-electrocyclization to form nitronate intermediates, which can be captured through tandem [3 + 2] dipolar cycloadditions to form highly functionalized nitroso acetals. The one-pot, two-step domino process is highly efficient, proceeding with good facial selectivity and exoselectivity. Dipolarophiles featuring electron-rich, -neutral, and -deficient carbon-carbon double bonds are viable substrates for [3 + 2] cycloadditions with the in situ generated nitronates. In addition, the highly functionalized nitroso acetal products can be hydrogenolyzed selectively to form densely functionalized spirocyclic hydroxy amides or hydroxy gamma-amino acids. |
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MeSH term(s) | Acetals/chemistry ; Cyclization ; Nitroso Compounds/chemistry ; Stereoisomerism |
Chemical Substances | Acetals ; Nitroso Compounds |
Language | English |
Publishing date | 2010-06-15 |
Publishing country | United States |
Document type | Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't |
ZDB-ID | 3155-0 |
ISSN | 1520-5126 ; 0002-7863 |
ISSN (online) | 1520-5126 |
ISSN | 0002-7863 |
DOI | 10.1021/ja1038819 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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