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

[1] Main group organometallics in organic synthesis [J].

Afarinkia, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2025-2046

[2] Aminolysis of Epoxides Using Iridium Trichloride as an Efficient Catalyst [J].

Agarwal, Jyoti ;

Duley, Anju ;

Rani, Rashmi ;

Peddinti, Rama Krishna .

SYNTHESIS-STUTTGART, 2009, (16) :2790-2796

[3] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[4] The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines [J].

Arai, Kenzo ;

Lucarini, Simone ;

Salter, Matthew M. ;

Ohta, Kentaro ;

Yamashita, Yasuhiro ;

Kobayashi, Shuj .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) :8103-8111

[5] Enantioselective desymmetrization of meso epoxides with anilines catalyzed by a niobium complex of a chiral multidentate binol derivative [J].

Arai, Kenzo ;

Salter, Matthew M. ;

Yamashita, Yasuhiro ;

Kobayashi, Shu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :955-957

[6] Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water [J].

Azoulay, S ;

Manabe, K ;

Kobayashi, S .

ORGANIC LETTERS, 2005, 7 (21) :4593-4595

[7] Insight into the mechanism of the asymmetric ring-opening aminolysis of 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane catalyzed by titanium/BINOLate/water system:: Evidence for the Ti(BINOLate)2-bearing active catalyst entities and the role of water [J].

Bao, Hongli ;

Zhou, Jing ;

Wang, Zheng ;

Guo, Yinlong ;

You, Tianpa ;

Ding, Kuiling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10116-10127

[8] Asymmetric aminolysis of aromatic epoxides:: A facile catalytic enantioselective synthesis of anti-β-amino alcohols [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Massaccesi, M ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2004, 6 (13) :2173-2176

[9] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[10]

Bolm C, 2001, SYNLETT, P1461

← 1 2 3 4 5 6 7 →