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Synthesis 2011(19): 3204-3207  
DOI: 10.1055/s-0030-1260175
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Method for the Stereoselective Synthesis of Thiiran-2-ylmethyl Alkylcarbamates

Andrey Shiryaev*a, Vadim Shiryaeva, Alexander Korlukovb, Daniya Khamitovab
a Samara State Technical University, Galaktionovskaya St. 244, 443100 Samara, Russian Federation
Fax: +7(846)3322122; e-Mail: andrey_shiryaev@yahoo.com;
b Nesmeyanov Institute of Organoelement Compounds, Vavilov St. 28, 119991 Moscow, Russian Federation
Further Information

Publication History

Received 7 June 2011
Publication Date:
18 August 2011 (online)

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Abstract

A highly efficient stereoselective conversion of N-alkyl-5-(acyloxymethyl)-1,3-oxathiolane-2-imines into thiiran-2-ylmethyl alkylcarbamates is described. The reaction is catalyzed by sodium methoxide and proceeds under mild conditions at room temperature in methanol.

Key words

thiiranes - imines - esters - tandem reaction - stereoselectivity

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