Synlett 2014; 25(12): 1697-1700
DOI: 10.1055/s-0034-1378203
letter
© Georg Thieme Verlag Stuttgart · New York

Convenient Access to Cycloalk-2-enone-Derived N-Sulfonyl Imines

Sebastian Hirner
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany   Fax: +49(6421)2825362   Email: zezschwitz@chemie.uni-marburg.de
,
Johannes Westmeier
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany   Fax: +49(6421)2825362   Email: zezschwitz@chemie.uni-marburg.de
,
Sandra Gebhardt
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany   Fax: +49(6421)2825362   Email: zezschwitz@chemie.uni-marburg.de
,
Christian H. Müller
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany   Fax: +49(6421)2825362   Email: zezschwitz@chemie.uni-marburg.de
,
Paultheo von Zezschwitz*
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany   Fax: +49(6421)2825362   Email: zezschwitz@chemie.uni-marburg.de
› Author Affiliations
Further Information

Publication History

Received: 24 February 2014

Accepted after revision: 02 May 2014

Publication Date:
28 May 2014 (online)


Preview

Abstract

The first synthesis of N-tosyl imines from various cyclopent-2-enones and cyclohex-2-enones was achieved by direct condensation with tosyl amide in the presence of TiCl(OEt)3 and Et3N. In addition, N-tert-butylsulfonyl imines from five- to seven-membered cycloalk-2-enones were obtained through formation of the ­respective oximes and subsequent Hudson reaction. These compounds are easy to handle solids and they are interesting starting materials for a variety of transformations.

Supporting Information