Enantioselective Ring Opening Reaction of meso-Epoxides with Aromatic and Aliphatic Amines Catalyzed by Magnesium Complexes of BINOL Derivatives

被引：50

作者：

Bao, Hongli ^{[1
,2
]}

Wu, Jiang ^{[1
]}

Li, Hongji ^{[1
]}

Wang, Zheng ^{[1
]}

You, Tianpa ^{[2
]}

Ding, Kuiling ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 35期

基金：

中国国家自然科学基金;

关键词：

Asymmetric catalysis; Epoxides; Amino alcohols; Amines; Magnesium; ASYMMETRIC AMINOLYSIS; 1,2-AMINO ALCOHOLS; CYCLOHEXENE OXIDE; CHIRAL CATALYST; TRIFLATE; DESYMMETRIZATION; EFFICIENT; ANILINES;

D O I：

10.1002/ejoc.201001222

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalyzed by the Mg complexes of BINOL derivatives, the enantioselective ring opening reaction of various meso-epoxides proceeded smoothly with either aromatic or aliphatic amines as the nucleophiles to afford the corresponding chiral beta-amino alcohols in moderate-to-high yields with good to excellent enantioselectivities.

引用

页码：6722 / 6726

页数：5

共 63 条

[41]

Ogawa C, 2005, HETEROCYCLES, V66, P201

[42]

Ogawa C, 2007, HETEROCYCLES, V72, P589

[43] Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines [J].

Ollevier, Thierry ;

Nadeau, Etienne .

TETRAHEDRON LETTERS, 2008, 49 (09) :1546-1550

[44] Asymmetric ring opening of epoxides [J].

Pastor, IM ;

Yus, M .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (01) :1-29

[45] Scandium triflate as an efficient and useful catalyst for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines under solvent-free conditions [J].

Placzek, AT ;

Donelson, JL ;

Trivedi, R ;

Gibbs, RA ;

De, SK .

TETRAHEDRON LETTERS, 2005, 46 (52) :9029-9034

[46] Catalytic asymmetric aminolysis of 3,5,8-trioxabicyclo [5.1.0]octane providing an optically pure 2-amino-1,3,4-butanetriol equivalent [J].

Sagawa, S ;

Abe, H ;

Hase, Y ;

Inaba, T .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4962-4965

[47] Scandium-bipyridine-catalyzed enantioselective addition of alcohols and amines to meso-epoxides [J].

Schneider, C ;

Sreekanth, AR ;

Mai, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (42) :5691-5694

[48] Synthesis of 1,2-difunctionalized fine chemicals through catalytic, enantioselective ring-opening reactions of epoxides [J].

Schneider, Christoph .

SYNTHESIS-STUTTGART, 2006, (23) :3919-3944

[49] An enantioselective formal synthesis of 4-demethoxydaunomycin using the catalytic asymmetric ring opening reaction of meso-epoxide with p-anisidine [J].

Sekine, A ;

Ohshima, T ;

Shibasaki, M .

TETRAHEDRON, 2002, 58 (01) :75-82

[50] The synthesis of a novel non-C2 symmetric H4-BINOL ligand and its application to titanium-catalyzed enantioselective addition of diethylzinc to aldehydes [J].

Shen, XQ ;

Guo, H ;

Ding, KL .

TETRAHEDRON-ASYMMETRY, 2000, 11 (21) :4321-4327

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