Enantioselective Synthesis of 1,4-Dihydrobenzoxathiins via Sulfoxide-Directed Borane Reduction

Abstract A novel sulfoxide-directed borane reduction was shown to give a variety of 2-substituted 1,4-dihydrobenzoxathiins. For all substrates evaluated, the reaction is completely stereospecific. Application of this methodology to the chiral synthesis of an artificial sweetener was demonstrated.

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2006-10, Vol.2006 (20), p.3389-3396
Main Authors: Waters, Marjorie S., Onofiok, Ekama, Tellers, David M., Chilenski, Jennifer R., Song, Zhiguo Jake
Format: Article
Language:English
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Description
Summary:Abstract A novel sulfoxide-directed borane reduction was shown to give a variety of 2-substituted 1,4-dihydrobenzoxathiins. For all substrates evaluated, the reaction is completely stereospecific. Application of this methodology to the chiral synthesis of an artificial sweetener was demonstrated.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950243