4.8 Article

Rhodium-Catalyzed Enantioselective Anti-Markovnikov Hydroformylation of α-Substituted Acryl Acid Derivatives

Journal

ORGANIC LETTERS
Volume 22, Issue 3, Pages 1108-1112

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04624

Keywords

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Funding

  1. National Natural Science Foundation of China [21871212, 21432007, 21672094]
  2. Natural Science Foundation of Hubei Province [2018CFB430]
  3. Science and Technology Innovation Committee of Shenzhen [JSGG20170821140353405, KQTD2015071710315717]
  4. Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
  5. SZDRC Discipline Construction Program

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Rhodium-catalyzed asymmetric anti-Markovnikov hydroformylation of alpha-substituted acrylates/acrylamides has been developed. By employing the Rh/(S,S)-DTBM-YanPhos complex, a series of beta-chiral linear aldehydes were obtained in high yields (up to 94% yield) and high enantioselectivities (up to 96% ee). The utility of this methodology is demonstrated by a gram-scale reaction and a concise synthetic route to chiral gamma-butyrolactone.

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