Journal
TETRAHEDRON LETTERS
Volume 53, Issue 44, Pages 5903-5906Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.08.091
Keywords
Umpolung; Amino acid; Electrophilic amination; Cascade reaction; Oxime
Categories
Funding
- Otsuka Pharmaceutical Co. Award in Synthetic Organic Chemistry, Japan
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Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.
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