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

Hiroki Mandai; Ryuhei Shiomoto; Kazuki Fujii; Koichi Mitsudo; Seiji Suga

doi:10.1021/acs.orglett.0c03956

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

Hiroki Mandai, Ryuhei Shiomoto, Kazuki Fujii, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	1169-1174
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.0c03956
Publication status	Published - Feb 19 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

abstract = "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. ",

author = "Hiroki Mandai and Ryuhei Shiomoto and Kazuki Fujii and Koichi Mitsudo and Seiji Suga",

note = "Funding Information: This research was partially supported by JSPS Kakenhi Grant No. JP19K05456. Publisher Copyright: {\textcopyright} Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

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doi = "10.1021/acs.orglett.0c03956",

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T1 - Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives

T2 - Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles

AU - Mandai, Hiroki

AU - Shiomoto, Ryuhei

AU - Fujii, Kazuki

AU - Mitsudo, Koichi

AU - Suga, Seiji

PY - 2021/2/19

Y1 - 2021/2/19

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

Abstract

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