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

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Publikationens författare: Sara Källström, Tiina Saloranta, Adriaan J. Minnaard, Reko Leino
Förläggare: PERGAMON-ELSEVIER SCIENCE LTD
Publiceringsår: 2007
Tidskrift: Tetrahedron Letters
Tidskriftsakronym: TETRAHEDRON LETT
Volym: 48
Nummer: 39
Artikelns första sida, sidnummer: 6958
Artikelns sista sida, sidnummer: 6961
Antal sidor: 4
ISSN: 0040-4039


Abstrakt

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.

Senast uppdaterad 2020-19-02 vid 01:48