253275-90-0Relevant articles and documents
Total synthesis of (+)-epoxyquinols A and B
Shoji, Mitsuru,Yamaguchi, Junichiro,Kakeya, Hideaki,Osada, Hiroyuki,Hayashi, Yujiro
, p. 3192 - 3194 (2007/10/03)
A highly stereoselective HfCl4-mediated Diels-Alder reaction of furan and the chiral acrylate ester of Corey's auxiliary to subsequently give 1, and the realization of the postulated biosynthetic pathway for the construction of epoxyquinols A a
A practical new chiral controller for asymmetric Diels-Alder and alkylation reactions
Sarakinos, Georgios,Corey
, p. 1741 - 1744 (2008/02/11)
(formula presented) The enantiomerically pure hydroxy sulfones (+)- and (-)-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55°C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+)- or (-)-2. Esters of (+)- and (-)-2 can be converted to Z-polassium enolates and alkylated with high face selectivity.