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Synthesis 2006(11): 1853-1857
DOI: 10.1055/s-2006-926469
DOI: 10.1055/s-2006-926469
PAPER
© Georg Thieme Verlag Stuttgart · New York
Anchimeric Assistance in the Case of Vicinal Dimesylate: Formation of Enantiomeric or meso-Bimorpholine
Further Information
Received
15 December 2005
Publication Date:
05 May 2006 (online)
Publication History
Publication Date:
05 May 2006 (online)
Abstract
An anchimeric effect of vicinal dimesylate in the intramolecular nucleophilic substitution by amine is described. One sulfonate group of the dimesylate acts as an internal nucleophile and the other as a leaving group, affording meso-bimorpholine in the intramolecular cyclization. ω,ω′-Dimesylate omits this effect and the target compound is obtained with high ee.
Key words
neighboring-group effects - cyclizations - asymmetric synthesis - amines - stereoselectivity
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