Indium- and zinc-mediated Barbier-type allylations of an N,N-(dimethylsulfamoyl)-protected aldimine and subsequent deprotection

A1 Journal article (refereed)


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Publication Details

List of Authors: Sara Källström, Tiina Saloranta, Adriaan J. Minnaard, Reko Leino
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Publication year: 2007
Journal: Tetrahedron Letters
Journal acronym: TETRAHEDRON LETT
Volume number: 48
Issue number: 39
Start page: 6958
End page: 6961
Number of pages: 4
ISSN: 0040-4039


Abstract

Barbier-type Zn and In-mediated allylations of an N,N-(dimethylsulfamoyl)-protected aldimine with different allyl bromides were investigated for the preparation of N-homoallylic sulfamides. The desired N,N-(dimethylsulfamoyl)-protected products were obtained in moderate to high yields in THF as the optimal solvent. Their further derivatization was demonstrated by a facile preparation of a functionalized dehydropiperidine by an allylation/olefin metathesis reaction sequence. A high yielding deprotection of the N,N-dimethylsulfamoyl group was likewise demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

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