Direct Spirocyclization from Keto-sulfonamides: An Approach to Azaspiro Compounds

Direct Spirocyclization from Keto-sulfonamides: An Approach to Azaspiro Compounds

Spontaneous spirocyclization of keto-sulfonamides via ynamides through a one-pot process is presented. Push–pull ynamides were obtained through Michael addition/elimination without Cu. The obtained azaspiro compounds are building blocks for indole alkaloids. Theoretical studies provide insights into...

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Bibliographic Details
Published in:Organic letters Vol. 19; no. 19; pp. 5042 - 5045
Main Authors: Beltran, Frédéric, Fabre, Indira, Ciofini, Ilaria, Miesch, Laurence
Format: Journal Article
Language:English
Published: United States American Chemical Society 06-10-2017
Subjects:
Chemical Sciences
Organic chemistry
Online Access:Get full text
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Summary:Spontaneous spirocyclization of keto-sulfonamides via ynamides through a one-pot process is presented. Push–pull ynamides were obtained through Michael addition/elimination without Cu. The obtained azaspiro compounds are building blocks for indole alkaloids. Theoretical studies provide insights into the mechanism of the formal Conia-ene reaction.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02216