4.8 Article

Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles

Journal

ORGANIC LETTERS
Volume 23, Issue 4, Pages 1169-1174

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03956

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Funding

  1. JSPS Kakenhi [JP19K05456]

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An efficient acylative kinetic resolution method for 3-hydroxy-3-substituted 2-oxindoles has been developed using a chiral DMAP derivative. The catalyst showed high efficiency with a wide range of substrates and could achieve high resolution within a short reaction time.
We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1'- binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3-9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.

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