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α ‐Oxymethyl Ketone Enolates for the Asymmetric Mannich Reaction. From Acetylene and N ‐Alkoxycarbonylimines to β ‐Amino Acids
Author(s) -
Palomo Claudio,
Oiarbide Mikel,
GonzálezRego M. Concepción,
Sharma Arun K.,
García Jesús M.,
González Alberto,
Landa Cristina,
Linden Anthony
Publication year - 2000
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(20000317)39:6<1063::aid-anie1063>3.0.co;2-y
Subject(s) - mannich reaction , trimethylsilyl , chemistry , ketone , acetylene , lithium (medication) , alkyl , organic chemistry , aldol reaction , medicinal chemistry , catalysis , medicine , endocrinology
The insufficient diastereoselectivity and generality , which are the main problems of the “acetate” aza – aldol reaction, can now be addressed through the reaction of the lithium enolate of endo ‐ O ‐trimethylsilyl acetyl isoborneol with various N ‐[( p ‐tolylsulfonyl)alkyl]carbamates (see scheme). This development provides record levels of asymmetric induction in a new Mannich‐type synthesis of β ‐amino acids which is general even for inherently enolizable imino compounds.