Highly Enantioselective Alk-2-enylation of Aldehydes through an Allyl-Transfer Reaction

Enantiopure homoallylic alcohols such as 1 (conveniently prepared from alk‐2‐enyl metal reagents with (−)‐ or (+)‐menthone) serve as alk‐2‐enyl donors to aldehydes. The allyl‐transfer reaction, which proceeds via a chairlike six‐membered‐ring transition state, gives the corresponding α adduct of the...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-03, Vol.42 (11), p.1273-1276
Main Authors: Nokami, Junzo, Nomiyama, Kenta, Matsuda, Seiji, Imai, Nobuyuki, Kataoka, Kazuhide
Format: Article
Language:English
Subjects:
alcohols
aldehydes
allylation
asymmetric synthesis
homogeneous catalysis
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Summary:Enantiopure homoallylic alcohols such as 1 (conveniently prepared from alk‐2‐enyl metal reagents with (−)‐ or (+)‐menthone) serve as alk‐2‐enyl donors to aldehydes. The allyl‐transfer reaction, which proceeds via a chairlike six‐membered‐ring transition state, gives the corresponding α adduct of the homoallylic alcohols, 2, in good yields with >99 % ee. pTSA=p‐toluenesulfonic acid.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200390327