Communication

Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade†

  1. Fang Li1,
  2. David Calabrese2,
  3. Matthew Brichacek2,
  4. Ivy Lin1,
  5. Prof. Jon T. Njardarson1,*

Article first published online: 10 JAN 2012

DOI: 10.1002/anie.201108261

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 8, pages 1938–1941, February 20, 2012

Additional Information

How to Cite

Li, F., Calabrese, D., Brichacek, M., Lin, I. and Njardarson, J. T. (2012), Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade. Angew. Chem. Int. Ed., 51: 1938–1941. doi: 10.1002/anie.201108261

Author Information

  1. 1

    Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)

  2. 2

    Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853-1301 (USA)

*Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)

  1. †

    We thank the NSF (CHE-0848324) and the University of Arizona for financial support.

Publication History

  1. Issue published online: 14 FEB 2012
  2. Article first published online: 10 JAN 2012
  3. Manuscript Received: 23 NOV 2011

Funded by

  • NSF. Grant Number: CHE-0848324
  • University of Arizona

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Keywords:

  • carbocycles;
  • cyclizations;
  • steroids;
  • sulfur heterocycles;
  • synthetic methods
Thumbnail image of graphical 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.

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