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Synthesis of Enantiopure Sulfonimidamides and Elucidation of Their Absolute Configuration by Comparison of Measured and Calculated CD Spectra and X-Ray Crystal Structure Determination

✍ Scribed by Christin Worch; Iuliana Atodiresei; Gerhard Raabe; Carsten Bolm

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 412 KB
Volume: 16
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200901715

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✦ Synopsis

Abstract

Straightforward syntheses of enantiopure N‐benzoyl‐ and N‐tert‐butyloxycarbonyl‐protected sulfonimidamides, which can be used as building blocks in newly designed catalysts, are presented. Key synthetic step is a dynamic resolution of a racemic sulfinic acid sodium salt. All subsequent transformations proceed stereospecifically. The absolute configurations at the sulfur atoms of both sulfonimidamides were determined by comparison of measured and calculated CD spectra. An X‐ray crystal structure determination of a sulfonimidoylguanidine derivative confirmed this result.

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