Journal
TETRAHEDRON LETTERS
Volume 50, Issue 26, Pages 3482-3484Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.03.020
Keywords
Ellman's auxiliary; tert-Butylsulfinamide; Sulfinimines; Deprotection; Cleavage; Dynamic kinetic resolution
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Funding
- Ministerio de Educacion y Ciencia
- Spanish Ministry of Education and Science
- CSIC
- DGI [CTQ2006-15515-CO2-01]
- GlaxoSmithKline
- EPSRC
- Higher Education Commission of Pakistan
- Royal Society for a Wolfson Research Merit Award
- Merck
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Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.
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