Is diazomethane addition to chiral α-keto esters subject to substrate diastereocontrol?

The uncatalyzed reaction of diazomethane with chiral benzoylformate esters results in the formation of alpha-oxiranyl esters without significant facial discrimination in almost every case. (c) 2006 Published by Elsevier Ltd.

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 11; pp. 1741 - 1744
Main Authors Petronijevic, Filip, Hart, Amy C., Paquette, Leo A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.03.2006
Elsevier
Subjects
[2+1]Cycloadditions
Asymmetric induction
Benzoylformate esters
Chemistry
Chemistry, Organic
Diastereoselective methylene transfer
Glycidic esters
Physical Sciences
Science & Technology
Diastereoselective methylene transfer
[2+1]Cycloadditions
Benzoylformate esters
Asymmetric induction
Glycidic esters
asymmetric induction
[2+1]cycloadditions
benzoylformate esters
glycidic esters
DERIVATIVES
diastereoselective methylene transfer
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More Information
Summary:The uncatalyzed reaction of diazomethane with chiral benzoylformate esters results in the formation of alpha-oxiranyl esters without significant facial discrimination in almost every case. (c) 2006 Published by Elsevier Ltd.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.12.137