Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade

Fang Li; David Calabrese; Matthew Brichacek; Ivy Lin; Jon T. Njardarson

doi:10.1002/anie.201108261

Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade

Fang Li, David Calabrese, Matthew Brichacek, Ivy Lin, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

The fifth element: An efficient new synthetic method for accessing 3,6-dihydro-2H-thiopyrans 1 in one pot has been developed. This method employs an anionic cascade, which is triggered by the addition of a vinyl nucleophile to a carbonyl group followed by S to O thiophosphate migration and an intramolecular thiolate displacement. The scope is demonstrated for a range of ketone and ester substrates.

Original language	English (US)
Pages (from-to)	1938-1941
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	8
DOIs	https://doi.org/10.1002/anie.201108261
State	Published - Feb 20 2012
Externally published	Yes

Keywords

carbocycles
cyclizations
steroids
sulfur heterocycles
synthetic methods

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201108261

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KW - cyclizations

KW - steroids

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KW - synthetic methods

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Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade

Abstract

Keywords

ASJC Scopus subject areas

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