共 11 条
Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates
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作者:

Xiao, Yinuo
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机构:
Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China

Li, Zhenpeng
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机构:
Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China

Xu, Changming
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h-index: 0
机构:
Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China
机构:
[1] Lanzhou Jiaotong Univ, Sch Chem & Chem Engn, Lanzhou 730070, Peoples R China
基金:
中国国家自然科学基金;
关键词:
Asymmetric alpha-alkylation;
Aryl acetates;
Phase-transfer catalysis;
Methylation;
Naproxen;
D O I:
10.1016/j.tetlet.2024.155347
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of alpha-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.
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共 11 条
[1]
Phase-transfer catalyzed asymmetric arylacetate alkylation
[J].
Andrus, Merritt B.
;
Harper, Kaid C.
;
Christiansen, Michael A.
;
Binkley, Meisha A.
.
TETRAHEDRON LETTERS,
2009, 50 (31)
:4541-4544

Andrus, Merritt B.
论文数: 0 引用数: 0
h-index: 0
机构:
Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

Harper, Kaid C.
论文数: 0 引用数: 0
h-index: 0
机构:
Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

Christiansen, Michael A.
论文数: 0 引用数: 0
h-index: 0
机构:
Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

Binkley, Meisha A.
论文数: 0 引用数: 0
h-index: 0
机构:
Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA
[2]
ACIDITIES OF THE H-C PROTONS IN CARBOXYLIC ESTERS, AMIDES, AND NITRILES
[J].
BORDWELL, FG
;
FRIED, HE
.
JOURNAL OF ORGANIC CHEMISTRY,
1981, 46 (22)
:4327-4331

BORDWELL, FG
论文数: 0 引用数: 0
h-index: 0

FRIED, HE
论文数: 0 引用数: 0
h-index: 0
[3]
Twenty years of naproxen technology
[J].
Harrington, PJ
;
Lodewijk, E
.
ORGANIC PROCESS RESEARCH & DEVELOPMENT,
1997, 1 (01)
:72-76

Harrington, PJ
论文数: 0 引用数: 0
h-index: 0
机构:
Syntex Grp, Ctr Technol, Boulder, CO 80301 USA Syntex Grp, Ctr Technol, Boulder, CO 80301 USA

Lodewijk, E
论文数: 0 引用数: 0
h-index: 0
机构:
Syntex Grp, Ctr Technol, Boulder, CO 80301 USA Syntex Grp, Ctr Technol, Boulder, CO 80301 USA
[4]
A simple catalytic route to naproxen
[J].
Kumar, S
;
Ramachandran, U
.
TETRAHEDRON-ASYMMETRY,
2005, 16 (03)
:647-649

Kumar, S
论文数: 0 引用数: 0
h-index: 0
机构:
NIPER, Dept Pharmaceut Technol, Mohali, Punjab, India NIPER, Dept Pharmaceut Technol, Mohali, Punjab, India

Ramachandran, U
论文数: 0 引用数: 0
h-index: 0
机构:
NIPER, Dept Pharmaceut Technol, Mohali, Punjab, India NIPER, Dept Pharmaceut Technol, Mohali, Punjab, India
[5]
Nickel-catalyzed asymmetric hydrogenation for the preparation of α-substituted propionic acids
[J].
Li, Bowen
;
Wang, Zhiling
;
Luo, Yicong
;
Wei, Hanlin
;
Chen, Jianzhong
;
Liu, Delong
;
Zhang, Wanbin
.
NATURE COMMUNICATIONS,
2024, 15 (01)

Li, Bowen
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

Wang, Zhiling
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

Luo, Yicong
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

Wei, Hanlin
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

Chen, Jianzhong
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

Liu, Delong
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Sch Pharm, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

Zhang, Wanbin
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
Shanghai Jiao Tong Univ, Sch Pharm, 800 Dongchuan Rd, Shanghai 200240, Peoples R China Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[6]
Proline-catalyzed asymmetric reactions
[J].
List, B
.
TETRAHEDRON,
2002, 58 (28)
:5573-5590

List, B
论文数: 0 引用数: 0
h-index: 0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
[7]
Enantioselective amino acid synthesis by chiral phase-transfer catalysis
[J].
Maruoka, K
;
Ooi, T
.
CHEMICAL REVIEWS,
2003, 103 (08)
:3013-3028

Maruoka, K
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

Ooi, T
论文数: 0 引用数: 0
h-index: 0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[8]
An efficient homogeneous catalytic enantioselective synthesis of α-amino acid derivatives
[J].
O'Donnell, MJ
;
Delgado, F
;
Hostettler, C
;
Schwesinger, R
.
TETRAHEDRON LETTERS,
1998, 39 (48)
:8775-8778

O'Donnell, MJ
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA

Delgado, F
论文数: 0 引用数: 0
h-index: 0
机构: Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA

Hostettler, C
论文数: 0 引用数: 0
h-index: 0
机构: Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA

Schwesinger, R
论文数: 0 引用数: 0
h-index: 0
机构: Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
[9]
Enantiodivergent Functionalization of Aryl Alkenes into Diverse Biarylalkanoic Acids by Integrating Biocatalytic Cascades with Chemocatalysis
[J].
See, Willy W. L.
;
Li, Zhi
.
ACS CATALYSIS,
2023, 13 (20)
:13215-13224

See, Willy W. L.
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117585, Singapore Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117585, Singapore

Li, Zhi
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117585, Singapore Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117585, Singapore
[10]
Development of C2-Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base
[J].
Xu, Changming
;
Qi, Yinsheng
;
Yang, Xinshuang
;
Li, Xiangfan
;
Li, Zhenpeng
;
Bai, Lei
.
ORGANIC LETTERS,
2021, 23 (08)
:2890-2894

Xu, Changming
论文数: 0 引用数: 0
h-index: 0
机构:
Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China

Qi, Yinsheng
论文数: 0 引用数: 0
h-index: 0
机构:
Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China

Yang, Xinshuang
论文数: 0 引用数: 0
h-index: 0
机构:
Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China

Li, Xiangfan
论文数: 0 引用数: 0
h-index: 0
机构:
Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China

Li, Zhenpeng
论文数: 0 引用数: 0
h-index: 0
机构:
Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China

Bai, Lei
论文数: 0 引用数: 0
h-index: 0
机构:
Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Peoples R China Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Peoples R China