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Synthesis 2004(9): 1413-1418  
DOI: 10.1055/s-2004-822376
PAPER
© Georg Thieme Verlag Stuttgart · New York

C-C Bond Formation via N-Phosphoryliminium Ions

Sape S. Kindermana, Jan H. van Maarseveena, Hans E. Schoemakera,c, Henk Hiemstra*a, Floris P. J. T. Rutjes*a,b
a J. H. van’t Hoff Institute of Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
b Department of Organic Chemistry, NSRIM, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
Fax: +31(24)365 3393; e-Mail: rutjes@sci.kun.nl;
c DSM Research, Life Science Products, PO Box 18, 6160 MD Geleen, The Netherlands
Further Information

Publication History

Received 15 April 2004
Publication Date:
18 May 2004 (online)

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Abstract

This paper describes preliminary results in the field of rather unexplored nucleophilic additions to N-phosphoryliminium ions. The synthesis of allylic and non-allylic cyclic amidophosphate-based N,O-acetals and their application in C-C bond formation is detailed. In addition, the influence of a chiral auxiliary on the phosphorus atom has been investigated.

Key words

amidophosphate - phosphoryliminium ion - N,O-acetal - ring-closing metathesis - alkoxyallene

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