Grignard Additions to Cyclic
Sulfamidate Imines: Synthesis of N-Substituted Quaternary Sulfamidate
Building Blocks

Stanley Chang; Ernest E. Lee

doi:10.1055/s-0029-1218778

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Synthesis 2010(14): 2361-2366
DOI: 10.1055/s-0029-1218778

PAPER

Grignard Additions to Cyclic Sulfamidate Imines: Synthesis of N-Substituted Quaternary Sulfamidate Building Blocks

Stanley Chang, Ernest E. Lee*
Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, QC, H9H 3L1, Canada
Fax: +1(514)4284939; e-Mail: ernest_lee@merck.com;

Further Information

Publication History

Received 18 January 2010
Publication Date:
05 May 2010 (online)

Abstract
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Abstract

The addition of Grignard reagents to cyclic sulfamidate imines has been developed as a facile method for the synthesis of N-substituted quaternary sulfamidates. By way of ring opening with an appropriate nucleophile, versatile synthons for 1,2-amino alcohols, 1,2-diamines, and β-amino acids are produced.

Key words

cyclic imine - Grignard addition - sulfamidate imine - N-substituted quaternary stereocenter

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