Urea derivative organocatalyzed enantioselective Friedel–Crafts alkylation of α-naphthols with isatins

Liming Wang; Zhe Chen; Huiting Jiang; Jie Zhang; Ying Jin

doi:10.1002/chir.23447

Urea derivative organocatalyzed enantioselective Friedel–Crafts alkylation of α-naphthols with isatins

Liming Wang
, Zhe Chen
, Huiting Jiang
, Jie Zhang
, Ying Jin

Health Science Center

Xi'an Jiaotong University
Jilin University

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

3 Scopus citations

Abstract

An organocatalytic enantioselective Friedel–Crafts alkylation of α-naphthols with isatin derivatives was catalyzed by Takemoto-type urea catalyst to give optical active 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles in 75%–92% yields with up to 95% enantiomeric excess (ee) value. The catalyst type and the substrate scope were broadened in this methodology.

Original language	English
Pages (from-to)	977-988
Number of pages	12
Journal	Chirality
Volume	34
Issue number	7
DOIs	https://doi.org/10.1002/chir.23447
State	Published - Jul 2022

Keywords

3-hydroxy-2-oxindoles
Takemoto-type catalyst
asymmetric
organocatalysis
α-naphthols

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10.1002/chir.23447

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title = "Urea derivative organocatalyzed enantioselective Friedel{\textendash}Crafts alkylation of α-naphthols with isatins",

abstract = "An organocatalytic enantioselective Friedel{\textendash}Crafts alkylation of α-naphthols with isatin derivatives was catalyzed by Takemoto-type urea catalyst to give optical active 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles in 75\%{\textendash}92\% yields with up to 95\% enantiomeric excess (ee) value. The catalyst type and the substrate scope were broadened in this methodology.",

keywords = "3-hydroxy-2-oxindoles, Takemoto-type catalyst, asymmetric, organocatalysis, α-naphthols",

author = "Liming Wang and Zhe Chen and Huiting Jiang and Jie Zhang and Ying Jin",

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year = "2022",

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doi = "10.1002/chir.23447",

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volume = "34",

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T1 - Urea derivative organocatalyzed enantioselective Friedel–Crafts alkylation of α-naphthols with isatins

AU - Wang, Liming

AU - Chen, Zhe

AU - Jiang, Huiting

AU - Zhang, Jie

AU - Jin, Ying

PY - 2022/7

Y1 - 2022/7

N2 - An organocatalytic enantioselective Friedel–Crafts alkylation of α-naphthols with isatin derivatives was catalyzed by Takemoto-type urea catalyst to give optical active 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles in 75%–92% yields with up to 95% enantiomeric excess (ee) value. The catalyst type and the substrate scope were broadened in this methodology.

AB - An organocatalytic enantioselective Friedel–Crafts alkylation of α-naphthols with isatin derivatives was catalyzed by Takemoto-type urea catalyst to give optical active 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles in 75%–92% yields with up to 95% enantiomeric excess (ee) value. The catalyst type and the substrate scope were broadened in this methodology.

KW - 3-hydroxy-2-oxindoles

KW - Takemoto-type catalyst

KW - asymmetric

KW - organocatalysis

KW - α-naphthols

UR - https://www.scopus.com/pages/publications/85128096091

U2 - 10.1002/chir.23447

DO - 10.1002/chir.23447

M3 - 文章

C2 - 35413136

AN - SCOPUS:85128096091

SN - 0899-0042

VL - 34

SP - 977

EP - 988

JO - Chirality

JF - Chirality

IS - 7

ER -

Urea derivative organocatalyzed enantioselective Friedel–Crafts alkylation of α-naphthols with isatins

Abstract

Keywords

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