137369-60-9Relevant academic research and scientific papers
C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Application and Synthesis of Naturally Occuring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide
Bonini, Carlo,Federici, Chiara,Rossi, Leucio,Righi, Giuliana
, p. 4803 - 4812 (1995)
The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly.In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or threo stereochemistry starting from trans or cis epoxy alcohols.Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occuring (S,S)-2,3-octanediol and (R,R)-muricatacin.The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides.The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols.This methodology has been applied to the asymmetric synthesis of naturally occuring pheromones like 3(R)-octanol and 4(R)-dodecanolide.
Highly Regioselective Ring Opening of 2,3-Epoxy Alcohol Methanesulfonates
Gao, Lian-xun,Saitoh, Hitoshi,Feng, Fei,Murai, Akio
, p. 1787 - 1790 (2007/10/02)
Reaction of 2,3-epoxy-1-ol methanesulfonates with diethylaluminum chloride or with the mixture of diethylaluminum chloride and diethylamine hydrobromide in dichloromethane gave rise to regioselectively the corresponding 3-chloro- and 3-bromo-1,2-diol 1-methanesulfonates, respectively, in excellent yields.
