4.8 Article

Synthesis of P-Stereogenic Phospholene Boranes via Asymmetric Deprotonation and Ring-Closing Metathesis

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ORGANIC LETTERS
卷 15, 期 1, 页码 192-195

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AMER CHEMICAL SOC
DOI: 10.1021/ol303253h

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  1. Givaudan
  2. Wild Fund
  3. University of York
  4. EU/Celtic Catalysts (Marie-Curie Transfer of Knowledge grant)

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The first examples of the asymmetric synthesis of P-stereogenic vinylic phospholene boranes are described. The synthetic approach is concise and flexible. The route involves (i) asymmetric deprotonation-allylation of a dimethyl phosphine borane; (ii) telescoped regioselective deprotonation, paraformaldehyde trapping, and hydroxyl group elimination to give a diene; and (iii) ring-closing metathesis.

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