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Dehydrative reduction: a highly diastereoselective synthesis of syn-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane. | LitMetric
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Dehydrative reduction: a highly diastereoselective synthesis of syn-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane.

Seongkon Kim Jane Y Wu Helen Y Chen Frank DiNinno

Org Lett

Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA.

Published: March 2003

TFA/Et(3)SiH-mediated cyclization of thioketones 5 derived from the reaction of functionalized thiophenols (catechols) with bromo ketones gave syn 2,3-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane 1 with total diastereoselectivity (>99:1), in excellent yields.

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http://dx.doi.org/10.1021/ol0274763DOI Listing

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