Catalytic asymmetric Henry reaction

被引：371

作者：

Boruwa, Joshodeep ^{[1
]}

Gogoi, Naminita ^{[1
]}

Saikia, Partha Pratim ^{[1
]}

Barua, Nabin C. ^{[1
]}

机构：

[1] CSIR, Nat Prod Chem Div, Reg Res Lab, Jorhat 785006, Assam, India

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 24期

关键词：

D O I：

10.1016/j.tetasy.2006.12.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The classical Henry reaction, the coupling of a nitroalkane with a carbonyl compound in the presence of a base, is an important C-C bond forming reaction in organic chemistry giving beta-nitroalcohols, which are useful synthons in organic synthesis. However, an asymmetric version of the reaction, that has been developed recently, gives a new dimension to the classical Henry reaction whereby the control of stereochemistry of two newly generated carbon centres has become possible. In this review, the various catalytic methods for this purpose are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3315 / 3326

页数：12

共 67 条

[1] Synthesis and applications of C2-symmetric guanidine bases [J].

Allingham, MT ;

Howard-Jones, A ;

Murphy, PJ ;

Thomas, DA ;

Caulkett, PWR .

TETRAHEDRON LETTERS, 2003, 44 (48) :8677-8680

[2] Chiral lanthanum-lithium-binaphthol complex covalently bonded to silica and MCM-41 for enantio selective nitroaldol (Henry) reaction [J].

Bhatt, AP ;

Pathak, K ;

Jasra, RV ;

Kureshy, RI ;

Khan, NUH ;

Abdi, SHR .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 244 (1-2) :110-117

[3] A highly efficient synthesis of the C-13 side-chain of taxol using Shibasaki's asymmetric Henry reaction [J].

Borah, JC ;

Gogoi, S ;

Boruwa, J ;

Kalita, B ;

Barua, NC .

TETRAHEDRON LETTERS, 2004, 45 (18) :3689-3691

[4] Stereoselective total synthesis of (+)-boronolide [J].

Boruwa, J ;

Barua, NC .

TETRAHEDRON, 2006, 62 (06) :1193-1198

[5]

Braunstein P, 2001, ANGEW CHEM INT EDIT, V40, P680, DOI 10.1002/1521-3773(20010216)40:4<680::AID-ANIE6800>3.0.CO

[6]

2-0

[7] ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION [J].

CHINCHILLA, R ;

NAJERA, C ;

SANCHEZAGULLO, P .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1393-1402

[8] Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters [J].

Christensen, C ;

Juhl, K ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4875-4881

[9] Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters [J].

Christensen, C ;

Juhl, K ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2001, (21) :2222-2223

[10] SILYL NITRONATES - IMPROVED NITRO-ALDOL REACTIONS AND REDUCTIVE ROUTES TO 2-AMINOALCOHOLS [J].

COLVIN, EW ;

SEEBACH, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :689-691

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