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Synthesis 2005(13): 2137-2142  
DOI: 10.1055/s-2005-869967
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of N-Protected Trisubstituted Oxazolidines from Ketones, Vinyl Ethers, and Fluoroalkanesulfonyl Azides in Mild Conditions

Ping Hea, Shizheng Zhu*a,b
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: zhusz@mail.sioc.ac.cn;
b College of Chemical Environment, South China Normal University, Guangzhou 510631, P. R. China
Further Information

Publication History

Received 27 January 2005
Publication Date:
20 June 2005 (online)

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Abstract

A facile one-step method has been developed for the synthesis of 2,3,5-trisubstituted oxazolidines in moderate yields by the three-component reaction of ketones, vinyl ethers, and fluoroalkanesulfonyl azides at 0 °C within five minutes. This practical synthetic method provides a convenient and expeditious access to N-per(poly)fluoroalkanesulfonyl oxazolidines.

Key words

fluoroalkanesulfonyl azide - ketone - vinyl ether - oxazolidine - multi-component reactions

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He, P.; Zhu, S. Z. Tetrahedron 2005, in press.

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CCDC number: CCDC 262795