Efficient Synthesis of Thiopyrans Using a Sulfur‐Enabled Anionic Cascade

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

Angewandte Chemie International Edition · 2012 · 22 citations · 22 references

Concepts

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.

References

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