Issue 1, 2011

Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction

Abstract

A highly diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction assisted by per(poly)fluoro-alkanesulfinamides is presented, providing a broad spectrum of highly functionalized piperidine derivatives with excellent endo/exo and facial diastereoselectivities. The electron-withdrawing perfluoroalkyl groups are crucial for the success of this reaction under mild conditions and facilitate monitoring the process and stereoselectivities of the reaction. The synthetic potential of these cycloadducts is also highlighted.

Graphical abstract: Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction

Supplementary files

Article information

Article type
Communication
Submitted
09 Sep 2010
Accepted
28 Oct 2010
First published
17 Nov 2010

Org. Biomol. Chem., 2011,9, 74-77

Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction

P. Li, L. Liu and J. Liu, Org. Biomol. Chem., 2011, 9, 74 DOI: 10.1039/C0OB00699H

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