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Olefinic cyclization promoted by beckmann rearrangement of oxime sulfonate synthesis of dl-muscone

✍ Scribed by Soichi Sakane; Keiji Maruoka; Hisashi Yamamoto

Book ID
104217044
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
203 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The acid-catalyzed cyclization of olefinic oxime mesylates has been successfully applied for the synthesis of g-muscone and related macrocycles.

We have recently shown that a double bond may become involved in the Lewis acid-catalyzed rearrangement of a suitably constituted olefinic oxime sulfonate and four distinct cyclization modes (Endo(endo, Endo(exo, Exe(B)-endo, Exe(B)-exo) were disclosed.' At the outset of these works, we were interested in the possibility that Endo cyclizations might serve as a powerful tool for ring-transformation reactions.

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