Lewis Acid-Mediated Highly Regioselective SN2-Type Ring-Opening of 2-Aryl-N-tosylazetidines and Aziridines by Alcohols

Manas K. Ghorai,* Kalpataru Das and Dipti Shukla

*Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India, Email: mkghoraiiitk.ac.in

M. K. Ghorai, K. Das, D. Shukla, J. Org. Chem., 2007, 72, 5859-5862.

DOI: 10.1021/jo0703294

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Abstract

A lewis acid-mediated highly regioselective S_N2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols afforded various 1,3-amino ethers in excellent yields. Similar S_N2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produces the corresponding nonracemic 1,2-amino ethers in excellent yields and good ee.

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Key Words

1,3-Aminoalcohols

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ID: J42-Y2007-2360