BF3·OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

Ghorai, Manas K. ; Kumar, Amit ; Tiwari, Deo Prakash (2010) BF3·OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides Journal of Organic Chemistry, 75 (1). pp. 137-151. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo902244y

Related URL: http://dx.doi.org/10.1021/jo902244y

Abstract

A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH(2)Cl(2) solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:117269
Deposited On:15 Apr 2021 10:47
Last Modified:15 Apr 2021 10:47

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