A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction

被引：488

作者：

Evans, DA ^{[1
]}

Seidel, D ^{[1
]}

Rueping, M ^{[1
]}

Lam, HW ^{[1
]}

Shaw, JT ^{[1
]}

Downey, CW ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 42期

关键词：

D O I：

10.1021/ja0373871

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction. Copyright © 2003 American Chemical Society.

引用

页码：12692 / 12693

页数：2

共 19 条

[1] 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
Christensen, C
Juhl, K
Hazell, RG
Jorgensen, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) : 4875 - 4881
[2] Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters
Christensen, C
Juhl, K
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2001, (21) : 2222 - 2223
[3] Corey EJ, 1999, ANGEW CHEM INT EDIT, V38, P1931, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO
[4] 2-4
[5] Concise synthesis of conformationally constrained pybox ligands
Davies, IW
Gerena, L
Lu, N
Larsen, RD
Reider, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9629 - 9630
[6] C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis
Ghosh, AK
Packiarajan, M
Cappiello, J
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (01) : 1 - 45
[7] Hathaway B.J. W. G., 1987, Comprehensive Coordination Chemistry, V5
[8] ELECTRONIC PROPERTIES AND STEREOCHEMISTRY OF MONO-NUCLEAR COMPLEXES OF COPPER(II) ION
HATHAWAY, BJ
BILLING, DE
[J]. COORDINATION CHEMISTRY REVIEWS, 1970, 5 (02) : 143 - &
[9] Chiral bis(oxazoline) copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions
Johnson, JS
Evans, DA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 325 - 335
[10] The Henry reaction: recent examples
Luzzio, FA
[J]. TETRAHEDRON, 2001, 57 (06) : 915 - 945

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