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Design and Evaluation of a Practical Camphor‐Based Methyl Ketone Enolate for Highly Stereoselective “Acetate” Aldol Reactions
Author(s) -
Palomo Claudio,
González Alberto,
García Jesús M.,
Landa Cristina,
Oiarbide Mikel,
Rodríguez Santiago,
Linden Anthony
Publication year - 1998
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/(sici)1521-3773(19980202)37:1/2<180::aid-anie180>3.0.co;2-4
Subject(s) - aldol reaction , diastereomer , ketone , aldehyde , stereoselectivity , camphor , electrophile , chemistry , organic chemistry , lithium (medication) , aldol condensation , methyl ketone , catalysis , biology , endocrinology
A trajectory close to the chiral auxiliary must be followed by the electrophilic aldehyde on attacking the lithium enolate of II . Consequently, unprecedented diastereomeric excesses in the 95–98% range are obtained for the aldol reaction of II with a variety of aldehydes. This is the first methyl ketone‐enolate strategy that allows recovery of the chiral controller of the process.