Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals

Xiaoqun Yang; Hongling Wang; Zhichao Jin; Yonggui Robin Chi

doi:10.1016/j.gresc.2021.05.002

Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals

Xiaoqun Yang, Hongling Wang, Zhichao Jin^*, Yonggui Robin Chi^*

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

A novel type of chiral oxidants are developed for efficient and enantioselective β-hydroxylation reaction of enals. The chiral oxidants can be easily obtained from readily available and inexpensive substituted benzoic acids and chiral prolinols. A commercially accessible and inexpensive achiral NHC catalyst is used for this catalytic approach. β-Hydroxyl esters bearing various substituents and substitution patterns are afforded as the final products in moderate to excellent yields and enantioselectivities.

Original language	English
Pages (from-to)	295-298
Number of pages	4
Journal	Green Synthesis and Catalysis
Volume	2
Issue number	3
DOIs	https://doi.org/10.1016/j.gresc.2021.05.002
Publication status	Published - Aug 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 The Authors

ASJC Scopus Subject Areas

Biotechnology
Catalysis

Keywords

Asymmetric β-hydroxylation
Chiral oxidant
N-Heterocyclic carbene
Organocatalysis
Radical reaction

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10.1016/j.gresc.2021.05.002

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title = "Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals",

abstract = "A novel type of chiral oxidants are developed for efficient and enantioselective β-hydroxylation reaction of enals. The chiral oxidants can be easily obtained from readily available and inexpensive substituted benzoic acids and chiral prolinols. A commercially accessible and inexpensive achiral NHC catalyst is used for this catalytic approach. β-Hydroxyl esters bearing various substituents and substitution patterns are afforded as the final products in moderate to excellent yields and enantioselectivities.",

keywords = "Asymmetric β-hydroxylation, Chiral oxidant, N-Heterocyclic carbene, Organocatalysis, Radical reaction",

author = "Xiaoqun Yang and Hongling Wang and Zhichao Jin and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2021 The Authors",

year = "2021",

month = aug,

doi = "10.1016/j.gresc.2021.05.002",

language = "English",

volume = "2",

pages = "295--298",

journal = "Green Synthesis and Catalysis",

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TY - JOUR

T1 - Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals

AU - Yang, Xiaoqun

AU - Wang, Hongling

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2021/8

Y1 - 2021/8

N2 - A novel type of chiral oxidants are developed for efficient and enantioselective β-hydroxylation reaction of enals. The chiral oxidants can be easily obtained from readily available and inexpensive substituted benzoic acids and chiral prolinols. A commercially accessible and inexpensive achiral NHC catalyst is used for this catalytic approach. β-Hydroxyl esters bearing various substituents and substitution patterns are afforded as the final products in moderate to excellent yields and enantioselectivities.

AB - A novel type of chiral oxidants are developed for efficient and enantioselective β-hydroxylation reaction of enals. The chiral oxidants can be easily obtained from readily available and inexpensive substituted benzoic acids and chiral prolinols. A commercially accessible and inexpensive achiral NHC catalyst is used for this catalytic approach. β-Hydroxyl esters bearing various substituents and substitution patterns are afforded as the final products in moderate to excellent yields and enantioselectivities.

KW - Asymmetric β-hydroxylation

KW - Chiral oxidant

KW - N-Heterocyclic carbene

KW - Organocatalysis

KW - Radical reaction

UR - http://www.scopus.com/inward/record.url?scp=85118656177&partnerID=8YFLogxK

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U2 - 10.1016/j.gresc.2021.05.002

DO - 10.1016/j.gresc.2021.05.002

M3 - Article

AN - SCOPUS:85118656177

SN - 2666-5549

VL - 2

SP - 295

EP - 298

JO - Green Synthesis and Catalysis

JF - Green Synthesis and Catalysis

IS - 3

ER -

Development of green and low-cost chiral oxidants for asymmetric catalytic hydroxylation of enals

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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