Highly Enantio- and Diastereoselective One-Pot Synthesis of Acyclic Epoxy Alcohols with Three Contiguous Stereocenters

Alice E. Lurain, Aaron Maestri, Ann Rowley Kelly, Patrick J. Carroll, and Patrick J. Walsh*
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323
J. Am. Chem. Soc., 2004, 126 (42), pp 13608–13609
DOI: 10.1021/ja046750g
Publication Date (Web): October 5, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pwalsh@sas.upenn.edu

Abstract

Abstract Image

Two highly enantio- and diastereoselective one-pot procedures for the synthesis of epoxy alcohols with up to three contiguous stereocenters are reported. Route one involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective epoxidation. Route two entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective epoxidation. The oxidant for the epoxidation is generated by exposure of the allylic alkoxide intermediate and the remaining organozinc reagent to dioxygen. Upon addition of catalytic titanium tetraisopropoxide, the directed epoxidation yields the epoxy alcohols with good to excellent yields.

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History

  • Published In Issue October 27, 2004
  • Received June 2, 2004 

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