99666-03-2Relevant academic research and scientific papers
Access to Unsaturated Chiral Epoxides. Part. III: Synthesis of a Component of the Sex Pheromone of Boarmia selenaria
Soulie, J.,Pericaud, F.,Lallemand, J.Y.
, p. 1367 - 1374 (2007/10/02)
A general method for the synthesis of chiral cis epoxides, which we have previously described, is used to synthetize the active enantiomer 1 of the sex pheromone of Boarmia selenaria
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
Selective Transformation of 2,3-Epoxy Alcohols and Related Derivatives. Strategies for Nucleophilic Attack at Carbon-1
Behrens, Carl H.,Ko, Soo Y.,Sharpless, K. Barry,Walker, Frederick J.
, p. 5687 - 5696 (2007/10/02)
In connection with the continuing recent interest in the stereoselective synthesis of epoxy alcohols, a systematic investigation of the bimolecular nucleophilic ring-opening reactions of acyclic 2,3-epoxy alcohols was undertaken.Strategies for nucleophilic attack at C-1 of a 2,3-epoxy alcohol, each of which depends upon the regioselective ring-opening of a 1,2-epoxy 3-ol, were explored.Under Payne rearrangement conditions, t-BuSNa was found to react with 2,3-epoxy alcohols to afford 1-tert-butylthio 2,3-diols.These diols can be readily converted to 1,2-epoxy 3-ols via S-alkylation followed by treatment with base.Alternatively, 1,2-epoxy 3-ols can be prepared from 2,3-epoxy alcohols by sulfonylation and acidic hydrolysis followed by ring-closure of the diol sulfonate intermediate.Dialkylamines were also found to react selectively with 2,3-epoxy alcohols under Payne rearrangement conditions to afford 1-amino 2,3-diols.
