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Paper | Special issue | Vol 76, No. 1, 2008, pp.569-581
Published online, 21st April, 2008
DOI: 10.3987/COM-08-S(N)45
Stereoselective Synthesis of Pyrrolidin-3-ols from Homoallylamines

Mohamed Medjahdi, José C. González-Gómez, Francisco Foubelo,* and Miguel Yus*

*Department of Organic Chemistry, Faculty of Science, and Institut of Organic Synthesis (ISO), University of Alicante, Apdo. 99, 03080 Alicante, Spain

Abstract

The reaction of enantiomerically pure N-tert-butylsulfinylhomoallylamines 3 (easily prepared by indium mediated allylation of the corresponding N-tert-butylsulfinylaldimine with allyl bromide) with MCPBA in CH2Cl2 at 25 °C leads to epoxysulfonamide derivatives 4 as a ca. 1:1 mixture of diastereoisomers. Cyclization of compounds 4 under basic conditions (K2CO3 in DMF) affords cis- and trans-pyrrolidin-3-ols 5 and 6, respectively.