Highly Enantioselective Alk‐2‐enylation of Aldehydes through an Allyl‐Transfer Reaction | Zendy

Nokami Junzo | Zendy; Nomiyama Kenta | Zendy; Matsuda Seiji | Zendy; Imai Nobuyuki | Zendy; Kataoka Kazuhide | Zendy

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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.

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