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

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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade'. Together they form a unique fingerprint.

  • Cite this