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Enantioselective Organocatalytic Direct Aldol Reactions of α‐Oxyaldehydes: Step One in a Two‐Step Synthesis of Carbohydrates
Author(s) -
Northrup Alan B.,
Mangion Ian K.,
Hettche Frank,
MacMillan David W. C.
Publication year - 2004
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.200453716
Subject(s) - aldol reaction , enantioselective synthesis , chemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis
Two‐faced : α‐Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereocontrolled production of erythrose (see scheme) architecture and sets the stage for a two‐step enantioselective synthesis of carbohydrates.