100229-48-9Relevant academic research and scientific papers
Controlled Payne Rearrangements of 2,3-Epoxy Alcohols in Aprotic Media: an Enantioselective Total Synthesis of (+)-exo-Brevicomin
Page, Philip C. Bulman,Rayner, Christopher M.,Sutherland, Ian O.
, p. 356 - 358 (1988)
The catalysis of the isomerisation of primary cis-2,3-epoxy alcohols to threo-1,2-epoxy alcohols by lithium chloride in tetrahydrofuran solution is described; the more reactive terminal epoxides may be selectively trapped in situ by reaction with nucleophiles, and this methodology is used in an enantioselective synthesis of (+)-exo-brevicomin.
Isomer Selectivity in Stereocontrolled Payne Rearrangement-epoxide Cleavage of 2,3-Epoxy Alcohols in Aprotic Solvents: Application to an Enantioselective Total Synthesis of (+)-exo-Brevicomin
Page, Philip C. Bulman,Rayner, Christopher M.,Sutherland, Ian O.
, p. 1375 - 1382 (2007/10/02)
Organo-copper and -cuprate reagents may be used to trap the more reactive epoxy alkoxide isomer in a Lewis acid-catalysed Payne rearrangement process.This methodology has been used as the key step in a five-step enantioselective total synthesis of (+)-exo
