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Catalytic Enantioselective and Diastereoselective Addition of Aldehyde‐Derived Enecarbamates to α‐Oxo Aldehydes
Author(s) -
Matsubara Ryosuke,
Kawai Nobuyuki,
Kobayashi Shū
Publication year - 2006
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.200600471
Subject(s) - enantioselective synthesis , aldehyde , catalysis , chemistry , organic chemistry , copper
Added benefits : Catalytic enantio‐ and diastereoselective addition of aldehyde‐derived enecarbamates to aldehydes is reported (see scheme). A copper(I)–diimine complex works well as the catalyst and the catalyst loading is not more than 1 mol % in most cases. By taking advantage of this reaction, the total synthesis of (2 S ,3 S ,4 S )‐3‐hydroxy‐4‐methylproline has been accomplished.