Chiral Cyclometalated Oxazoline Gold(III) Complex-Catalyzed Asymmetric Carboalkoxylation of Alkynes

Jia Jun Jiang; Jian Fang Cui; Bin Yang; Yulu Ning; Nathanael Chun Him Lai; Man Kin Wong

doi:10.1021/acs.orglett.9b02171

Chiral Cyclometalated Oxazoline Gold(III) Complex-Catalyzed Asymmetric Carboalkoxylation of Alkynes

Jia Jun Jiang
, Jian Fang Cui
, Bin Yang
, Yulu Ning
, Nathanael Chun Him Lai
, Man Kin Wong (Corresponding Author)

The Hong Kong Polytechnic University

Research output: Journal article publication › Journal article › Academic research › peer-review

40 Citations (Scopus)

Abstract

Asymmetric catalysis by using novel chiral O,O′-chelated 4,4′-biphenol cyclometalated oxazoline gold(III) complexes has been developed. A high yield (≤89%) and a high enantioselectivity (≤90% ee) were achieved in asymmetric carboalkoxylation of alkynes. Enantioselectivity could be significantly improved from 19% to 90% ee by increasing the steric size of the substituent on the chiral oxazoline ligand. Catalytically active Au^III species and the origin of chiral induction are proposed.

Original language	English
Pages (from-to)	6289-6294
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.9b02171
Publication status	Published - 16 Aug 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b02171

http://hdl.handle.net/10397/89276

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title = "Chiral Cyclometalated Oxazoline Gold(III) Complex-Catalyzed Asymmetric Carboalkoxylation of Alkynes",

abstract = "Asymmetric catalysis by using novel chiral O,O′-chelated 4,4′-biphenol cyclometalated oxazoline gold(III) complexes has been developed. A high yield (≤89\%) and a high enantioselectivity (≤90\% ee) were achieved in asymmetric carboalkoxylation of alkynes. Enantioselectivity could be significantly improved from 19\% to 90\% ee by increasing the steric size of the substituent on the chiral oxazoline ligand. Catalytically active AuIII species and the origin of chiral induction are proposed.",

author = "Jiang, \{Jia Jun\} and Cui, \{Jian Fang\} and Bin Yang and Yulu Ning and Lai, \{Nathanael Chun Him\} and Wong, \{Man Kin\}",

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doi = "10.1021/acs.orglett.9b02171",

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AU - Jiang, Jia Jun

AU - Cui, Jian Fang

AU - Yang, Bin

AU - Ning, Yulu

AU - Lai, Nathanael Chun Him

AU - Wong, Man Kin

PY - 2019/8/16

Y1 - 2019/8/16

N2 - Asymmetric catalysis by using novel chiral O,O′-chelated 4,4′-biphenol cyclometalated oxazoline gold(III) complexes has been developed. A high yield (≤89%) and a high enantioselectivity (≤90% ee) were achieved in asymmetric carboalkoxylation of alkynes. Enantioselectivity could be significantly improved from 19% to 90% ee by increasing the steric size of the substituent on the chiral oxazoline ligand. Catalytically active AuIII species and the origin of chiral induction are proposed.

AB - Asymmetric catalysis by using novel chiral O,O′-chelated 4,4′-biphenol cyclometalated oxazoline gold(III) complexes has been developed. A high yield (≤89%) and a high enantioselectivity (≤90% ee) were achieved in asymmetric carboalkoxylation of alkynes. Enantioselectivity could be significantly improved from 19% to 90% ee by increasing the steric size of the substituent on the chiral oxazoline ligand. Catalytically active AuIII species and the origin of chiral induction are proposed.

UR - https://www.scopus.com/pages/publications/85070855970

U2 - 10.1021/acs.orglett.9b02171

DO - 10.1021/acs.orglett.9b02171

M3 - Journal article

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AN - SCOPUS:85070855970

SN - 1523-7060

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EP - 6294

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Chiral Cyclometalated Oxazoline Gold(III) Complex-Catalyzed Asymmetric Carboalkoxylation of Alkynes

Abstract

ASJC Scopus subject areas

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