1021153-87-6Relevant articles and documents
Enzymatic resolution of chlorohydrins for the synthesis of enantiomerically enriched 2-vinyloxiranes
McCubbin, J. Adam,Maddess, Matthew L.,Lautens, Mark
, p. 289 - 293 (2008/12/21)
A series of vinylchlorohydrins are resolved by enzymatic kinetic resolution. The resulting R-alcohols, obtained in up to 99% ee, are stereoselectively converted into vinyloxiranes in high yield. The S-acetates, obtained in up to 99% ee were either deprotected to S-alcohols, or cyclized directly to vinyl oxiranes under basic conditions, with moderate to no loss in ee. The results are consistent with a racemization mechanism involving reversible migration of the acetate during deprotection. Georg Thieme Verlag Stuttgart.
