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Highly Enantioselective Alk‐2‐enylation of Aldehydes through an Allyl‐Transfer Reaction
Author(s) -
Nokami Junzo,
Nomiyama Kenta,
Matsuda Seiji,
Imai Nobuyuki,
Kataoka Kazuhide
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390327
Subject(s) - enantiopure drug , chemistry , enantioselective synthesis , reagent , menthone , adduct , ring (chemistry) , organic chemistry , baylis–hillman reaction , catalysis , menthol
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. p TSA= p ‐toluenesulfonic acid.