Journal
ORGANIC LETTERS
Volume 16, Issue 14, Pages 3840-3843Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol501892a
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- NSF [CHE-0967814]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0967814] Funding Source: National Science Foundation
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The asymmetric allylboration of N-H aldimines with optically pure trans-4-substituted-2-boryl-1,3-dienes 6 is described. These organoboranes 6 serve as near-perfect asymmetric allylborating agents for N-H R aldimines for the preparation of anti-1,2-disubstituted-3,4-pentadien-1-amines 11 as essentially single diastereomers in enantiomerically pure form (>98% de, >= 98% ee). Enantiomerically pure cis-2,3-disubstitued piperidines 12 and alpha,beta-disubstituted-beta-amino acids 17 are readily prepared through the standard protocols. A novel Ru-catalyzed hydroamination provides trans-4,5-disubstituted-1-pyrrolines 21 from 11.
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