Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 10, Pages 3272-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja100607z
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Funding
- NIH National Institute of Neurological Disorders and Stroke [NS-12389]
- Takeda Pharmaceutical Co.
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A useful enantioselective synthesis of angularly substituted 1-azabicyclic molecules that delivers the bicyclic amine products in good yield and 99% ee is reported. Angularly substituted cis-octahydrocyclopenta[b]pyrroles, cis-octahydroindoles. cis-decahydrocyclohepta[b]pyrroles. and cis-octahydrocyclopenta[b]pyridine are formed in good yields and 99% ee exclusively as the cis stereoisomers. Decahydroquinolines are generated as mixtures of cis and trans stereoisomers in similarly high cc. The starting materials for this cascade transformation are assembled in five steps from cycloalkanones and enantiomerically pure (R)-2-phenyl-3-butenamine. This enantioselective synthesis introduces a new strategy for dynamic kinetic resolution in which a rapid tautomeric equilibration of diastereomeric iminium cations is combined with a diastereoselective sigmatropic rearrangement.
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