Asymmetric Hydrogenation via Capture of Active Intermediates Generated from Aza-Pinacol Rearrangement

An efficient palladium-catalyzed asymmetric hydrogenation via capture of an active intermediate generated in situ from acid-catalyzed aza-Pinacol rearrangement has been successfully developed, providing efficient access to chiral exocyclic amines with up to 98% ee. Three-, four-, and five-membered c...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-11, Vol.136 (45), p.15837-15840
Main Authors: Yu, Chang-Bin, Huang, Wen-Xue, Shi, Lei, Chen, Mu-Wang, Wu, Bo, Zhou, Yong-Gui
Format: Article
Language:English
Subjects:
Amines - chemistry
Amino Alcohols - chemistry
Aza Compounds - chemistry
Catalysis
Hydrogenation
Oligopeptides - chemistry
Palladium - chemistry
Stereoisomerism
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Summary:An efficient palladium-catalyzed asymmetric hydrogenation via capture of an active intermediate generated in situ from acid-catalyzed aza-Pinacol rearrangement has been successfully developed, providing efficient access to chiral exocyclic amines with up to 98% ee. Three-, four-, and five-membered cyclic N-sulfonyl amino alcohols are viable substrates. This study opens a new window to the application of asymmetric hydrogenation.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5075745