Title of article :
syn-2,3-Disubstituted-2,3-dihydro-1,4-benzoxathiin rings: preparation from quinone ketals and 2-mercaptoethanols
Author/Authors :
Dormer، نويسنده , , Peter G. and Kassim، نويسنده , , Amude M. and Leazer Jr.، نويسنده , , Johnnie L. and Lang، نويسنده , , Fengrui and Xu، نويسنده , , Feng and Savary، نويسنده , , Kimberly A. and Corley، نويسنده , , Edward G. and DiMichele، نويسنده , , Lisa and DaSilva، نويسنده , , Jimmy O. and King، نويسنده , , Anthony O. and Tschaen، نويسنده , , David M. and Larsen، نويسنده , , Robert D.، نويسنده ,
Abstract :
A general method for the preparation of syn-2,3-disubstituted-2,3-dihydro-1,4-benzoxathiin rings from 2-mercaptoethanols and quinone ketals is presented. This ring system is produced by Michael addition of a 2-mercaptoethanol to a quinone ketal, followed by cyclization of the initial Michael adduct, and subsequent aromatization to afford a syn-2,3-disubstituted-1,4-benzoxathiin in fair to good chemical yield. Several chiral syn-2,3-disubstituted-2,3-dihydro-1,4-benzoxathiin rings were prepared with this method from enantioenriched 2-mercaptoethanols. No loss of enantiopurity was observed.
Keywords :
Michael addition , Quinone ketal , 2 , 3-dihydro-1 , 2-Mercaptoethanol , 4-Benzoxathiin
