165883-65-8Relevant academic research and scientific papers
Highly enantioselective ylide-mediated synthesis of terminal epoxides
Piccinini, Alessandro,Kavanagh, Sarah A.,Connon, Stephen J.
supporting information; experimental part, p. 7814 - 7816 (2012/09/05)
The highly efficient asymmetric epoxidation of aldehydes by methylene transfer is now possible using new sulfonium salts. This journal is
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.
A concise enantioselective strategy to (+)-(R)-goniothalamin and (+)-(R)-goniothalamin oxide by employing hydrolytic kinetic resolution and ring-closing metathesis as key steps
Bose, D. Subhas,Reddy, A. V. Narsimha,Srikanth, Bingi
body text, p. 2323 - 2326 (2009/04/04)
An efficient and general strategy to (R)-goniothalamin and (R)-goniothalamin oxide is described by using Jacobsen's hydrolytic kinetic resolution of racemic epoxide and ring-closing metathesis (RCM) as key steps, which provided a rapid access to these natural products that display a fascinating array of biological activity. (R)-Goniothalamin oxide was prepared in high yield and diastereomeric excess under various epoxidation conditions. Georg Thieme Verlag Stuttgart.
