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Stereoselective Alkylation of Sulfoxides and Sulfones Derived from (R)-Cysteine

✍ Scribed by Dehmlow, Eckehard Volker ;Pieper, Stefanie ;Neumann, Beate ;Stammler, Hans-Georg

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 664 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970533

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✦ Synopsis

Abstract

(R)‐Cysteinol was protected as its oxazoline derivatives 1a–c and oxidized to the sulfoxides 2, 3 and the sulfone 7. These compounds could be alkylated under chelate control to give tertiary and quaternary stereogenic centers in a highly stereoselective manner to yield 4a–c,5, 8a–c, 11 and 12. Starting with the sulfone 7, both configurations at the new chiral center can be constructed.

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