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

38 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

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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

UR - https://www.scopus.com/pages/publications/77956380991

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

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Keywords

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