Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes

Gold and silver: A 1:2 mixture of [{(S)‐1}(AuCl)2] and AgBF4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3‐disubstituted allenes with N‐unsubstituted carbamates to form N‐allylic carbamates in good yield, with high regio‐ and diastereoselectivity, and up to 92 % ee (see scheme...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-05, Vol.51 (21), p.5175-5178
Main Authors: Butler, Kristina L., Tragni, Michele, Widenhoefer, Ross A.
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
allenes
Amination
asymmetric catalysis
asymmetric synthesis
Catalysis
Gold
Gold - chemistry
hydroamination
Silver
Stereoisomerism
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Summary:Gold and silver: A 1:2 mixture of [{(S)‐1}(AuCl)2] and AgBF4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3‐disubstituted allenes with N‐unsubstituted carbamates to form N‐allylic carbamates in good yield, with high regio‐ and diastereoselectivity, and up to 92 % ee (see scheme, Cbz=benzyloxycarbonyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201584