4.8 Article

Catalytic Asymmetric Bromocyclization of Polyenes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 4, Pages 1460-1463

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b13193

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Funding

  1. ACT-C, JST
  2. JSPS
  3. Grants-in-Aid for Scientific Research [16F16041] Funding Source: KAKEN

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The first catalytic asymmetric bromonium ion-induced polyene cyclization has been achieved by using a chiral BINOL-derived thiophosphoramide catalyst and 1,3-dibromo-5,5-dimethylhydantoin as an electrophilic bromine source. Bromocyclization products are obtained in high yields, with good enantiomeric ratios and high diastereoselectivity, and are abundantly found as scaffolds in natural products.

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