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
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.0c03956
Publication status	Accepted/In press - 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c03956

Fingerprint Dive into the research topics of 'Kinetic resolution of tertiary alcohols by chiral DMAP derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles'. Together they form a unique fingerprint.

Cite this

@article{afc340f7c7e74aa483079e6d52af9457,

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.",

year = "2021",

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

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

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

N1 - Funding Information: This research was partially supported by JSPS Kakenhi Grant No. JP19K05456.

PY - 2021

Y1 - 2021

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85099090373&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85099090373&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c03956

DO - 10.1021/acs.orglett.0c03956

M3 - Article

AN - SCOPUS:85099090373

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -