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, Email: pwalshsas.upenn.edu

A. E. Lurain, A. Maestri, A. R. Kelly, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2004, 126, 13608-13609.

DOI: 10.1021/ja046750g

Abstract

Highly enantio- and diastereoselective one-pot procedures for the synthesis of epoxy alcohols involve either asymmetric addition of an alkylzinc reagent to an enal or asymmetric vinylation of an aldehyde with divinylzinc reagents. Exposure of the reaction mixtures to dioxygen and addition of catalytic titanium tetraisopropoxide yields epoxy alcohols with good to excellent yields.

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Highly Enantio- and Diastereoselective One-Pot Synthesis of Acyclic Epoxy Alcohols and Allylic Epoxy Alcohols

A.R. Kelly, A. E. Lurain, P. J. Walsh, J. Am. Chem. Soc., 2005, 127, 14668-14674.

DOI: 10.1021/ja051291k

Highly Enantio- and Diastereoselective Tandem Generation of Cyclopropyl Alcohols with up to Four Contiguous Stereocenters

H. Y. Kim, A. E. Lurain, P. Garcia-Carcia, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2005, 127, 13138-13139.

Asymmetric Addition of Alkylzinc Reagents to Cyclic α,β-Unsaturated Ketones and a Tandem Enantioselective Addition/Diastereoselective Epoxidation with Dioxygen

S.-J. Jeon, P. J. Walsh, J. Am. Chem. Soc., 2003, 125, 9544-9545.

Key Words

1,2-Addition, Epoxidation, Oxygen

ID: J48-Y2004-1780