A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins

Ying Xiang Gao; Le Chang; Hang Shi; Bo Liang; Kittiya Wongkhan; Duangduan Chaiyaveij; Andrei S. Batsanov; Todd B. Marder; Chuang Chuang Li; Zhen Yang; Yong Huanga

doi:10.1002/adsc.201000070

A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins

Ying Xiang Gao
, Le Chang
, Hang Shi
, Bo Liang
, Kittiya Wongkhan
, Duangduan Chaiyaveij
, Andrei S. Batsanov
, Todd B. Marder
, Chuang Chuang Li
, Zhen Yang
, Yong Huanga

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

39 Citations (Scopus)

Abstract

We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2- phenylsuccinates were obtained in >90% yield and up to 84% ee under optimized conditions.

Original language	English
Pages (from-to)	1955-1966
Number of pages	12
Journal	Advanced Synthesis and Catalysis
Volume	352
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.201000070
Publication status	Published - 2010
Externally published	Yes

Keywords

Asymmetric catalysis
Catalyst design
Enantioselectivity
Palladium thiourea-oxazoline library

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10.1002/adsc.201000070

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Gao, Y. X., Chang, L., Shi, H., Liang, B., Wongkhan, K., Chaiyaveij, D., Batsanov, A. S., Marder, T. B., Li, C. C., Yang, Z., & Huanga, Y. (2010). A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins. Advanced Synthesis and Catalysis, 352(11-12), 1955-1966. https://doi.org/10.1002/adsc.201000070

@article{49d76643baf94d45abab471ad4715012,

title = "A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins",

abstract = "We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2- phenylsuccinates were obtained in >90\% yield and up to 84\% ee under optimized conditions.",

keywords = "Asymmetric catalysis, Catalyst design, Enantioselectivity, Palladium thiourea-oxazoline library",

author = "Gao, \{Ying Xiang\} and Le Chang and Hang Shi and Bo Liang and Kittiya Wongkhan and Duangduan Chaiyaveij and Batsanov, \{Andrei S.\} and Marder, \{Todd B.\} and Li, \{Chuang Chuang\} and Zhen Yang and Yong Huanga",

year = "2010",

doi = "10.1002/adsc.201000070",

language = "English",

volume = "352",

pages = "1955--1966",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "11-12",

}

Gao, YX, Chang, L, Shi, H, Liang, B, Wongkhan, K, Chaiyaveij, D, Batsanov, AS, Marder, TB, Li, CC, Yang, Z & Huanga, Y 2010, 'A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins', Advanced Synthesis and Catalysis, vol. 352, no. 11-12, pp. 1955-1966. https://doi.org/10.1002/adsc.201000070

A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins. / Gao, Ying Xiang; Chang, Le; Shi, Hang et al.
In: Advanced Synthesis and Catalysis, Vol. 352, No. 11-12, 2010, p. 1955-1966.

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

TY - JOUR

T1 - A thiourea-oxazoline library with axial chirality

T2 - Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins

AU - Gao, Ying Xiang

AU - Chang, Le

AU - Shi, Hang

AU - Liang, Bo

AU - Wongkhan, Kittiya

AU - Chaiyaveij, Duangduan

AU - Batsanov, Andrei S.

AU - Marder, Todd B.

AU - Li, Chuang Chuang

AU - Yang, Zhen

AU - Huanga, Yong

PY - 2010

Y1 - 2010

N2 - We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2- phenylsuccinates were obtained in >90% yield and up to 84% ee under optimized conditions.

AB - We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2- phenylsuccinates were obtained in >90% yield and up to 84% ee under optimized conditions.

KW - Asymmetric catalysis

KW - Catalyst design

KW - Enantioselectivity

KW - Palladium thiourea-oxazoline library

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000281654500024

UR - https://openalex.org/W2075737712

U2 - 10.1002/adsc.201000070

DO - 10.1002/adsc.201000070

M3 - Journal Article

SN - 1615-4150

VL - 352

SP - 1955

EP - 1966

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-12

ER -

A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins

Abstract

Keywords

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