4.8 Article

Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C-H Activation/Cyclopropanation Cascade

Journal

ORGANIC LETTERS
Volume 21, Issue 22, Pages 9217-9222

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03589

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Funding

  1. National Natural Science Foundation of China [21672209, 21871253]
  2. National Basic Research Program of China [2015CB856600]

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Rhodium(III)-catalyzed annulative coupling of sulfoxonium ylides with allenoates was achieved, forming highly functionalized cyclopropanes with a quaternary carbon center by means of the sulfoxonium ylide functionality as a traceless bifunctional directing group and C4 synthon via an arene C-H activation and cyclopropanation cascade. The protocol features simultaneous formation of three new C-C bonds in one pot with excellent diastereoselectivity. The resultant cyclopropanation products could be further transformed to diverse synthetically useful compounds.

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