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 journalArticle

12 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1938-1941
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number8
DOIs
StatePublished - Feb 20 2012

Fingerprint

Nucleophiles
Ketones
Sulfur
Chemical elements
Esters
Substrates
thiopyran
thiophosphoric acid

Keywords

  • carbocycles
  • cyclizations
  • steroids
  • sulfur heterocycles
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade. / Li, Fang; Calabrese, David; Brichacek, Matthew; Lin, Ivy; Njardarson, Jon T.

In: Angewandte Chemie - International Edition, Vol. 51, No. 8, 20.02.2012, p. 1938-1941.

Research output: Contribution to journalArticle

Li, Fang ; Calabrese, David ; Brichacek, Matthew ; Lin, Ivy ; Njardarson, Jon T. / Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade. In: Angewandte Chemie - International Edition. 2012 ; Vol. 51, No. 8. pp. 1938-1941.
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