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Synlett 2006(19): 3352-3354
DOI: 10.1055/s-2006-951556
DOI: 10.1055/s-2006-951556
LETTER
© Georg Thieme Verlag Stuttgart · New York
A New Approach to the Stereoselective Carbodiazenylation of Olefins by Macrocyclization
Weitere Informationen
Received
26 July 2006
Publikationsdatum:
23. November 2006 (online)
Publikationsverlauf
Publikationsdatum:
23. November 2006 (online)
Abstract
The reduction of bisaryldiazonium salts in the presence of olefins leads to macrocyclic azo compounds. Chiral auxiliaries incorporated in the bisaryldiazonium salt allow the stereochemical control of the newly formed carbon center.
Key words
azo compounds - cyclizations - diastereoselectivity - macrocycles - radicals
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References and Notes
Our preliminary experiments have shown that the recovery of 3a from 5 is possible via Alloc-protection of the amine, esterification of the alcohol with 2-nitrobenzoic acid chloride and subsequent hydrogenation