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Synthesis 2007(15): 2273-2278
DOI: 10.1055/s-2007-966070
DOI: 10.1055/s-2007-966070
PAPER
© Georg Thieme Verlag Stuttgart · New York
Addition of Bis-sulfinyl Anions to Ketones: Stereoselective Synthesis of Allylic Alcohols through Evans-Mislow Rearrangement Based Domino Reactions
Further Information
Received
2 February 2007
Publication Date:
11 May 2007 (online)
Publication History
Publication Date:
11 May 2007 (online)
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Abstract
Enantiopure cyclic allylic alcohols were obtained from cyclic ketones and bis-sulfoxides through a domino reaction mixing anionic and concerted elementary steps. Total transfer of chirality was achieved, presumably through cooperative effects of both sulfoxides units. Depending on the ring size, both sulfinyl groups could be converted, giving C 2-symmetric bis-allylic alcohols.
Key words
alkenation - carbanion - pericyclic reaction - sulfoxide - sulfur
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