Enantioselective synthesis of 1, 4-dihydrobenzoxathiins via sulfoxide-directed borane reduction

MS Waters, E Onofiok, DM Tellers, JR Chilenski…

Index: Waters, Marjorie S.; Onofiok, Ekama; Tellers, David M.; Chilenski, Jennifer R.; Song, Zhiguo Jake Synthesis, 2006 , # 20 p. 3389 - 3396

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Citation Number: 2

Abstract

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.