Dehydrative reduction: a highly diastereoselective synthesis of syn-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane.
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.
Kim
Seongkon
S
Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA. seongkon_kim@merck.com
Wu
Jane Y
JY
Chen
Helen Y
HY
DiNinno
Frank
F
D002396:Catechols / Q000737:chemistry; D003500:Cyclization; D004146:Dioxanes / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D002396:Catechols; D004146:Dioxanes; D007659:Ketones