4.4 Article

Catalyst-Controlled Regio- and Stereoselective Bromolactonization with Chiral Bifunctional Sulfides

Journal

SYNLETT
Volume 30, Issue 14, Pages 1662-1666

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610716

Keywords

asymmetric synthesis; lactonization; organocatalysis; regioselectivity-; sulfides

Funding

  1. Japan Society for the Promotion of Science (JSPS) (KAKENHI) [JP19K05480]
  2. Cooperative Research Program of 'Network Joint Research Center for Materials and Devices' [20191310]
  3. Tokuyama Science Foundation
  4. Takahashi Industrial and Economic Research Foundation
  5. Shorai Foundation for Science and Technology

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Highly regioselective 5- exo bromolactonizations of stilbene-type carboxylic acids bearing electron-withdrawing substituents are achieved for the first time via the use of chiral bifunctional sulfide catalysts possessing a urea moiety. The chiral phthalide products are obtained in moderate to good enantioselectivities as the result of 5-exo cyclizations.

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