C2-symmetric Sc(III)-complexes chiral Lewis acids.: Catalytic enantioselective aldol additions glyoxylate esters

被引：70

作者：

Evans, DA ^{[1
]}

Masse, CE ^{[1
]}

Wu, J ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 20期

关键词：

D O I：

10.1021/ol026488l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Cationic Lewis acid complexes [Sc(pyridyl-bis(oxazolinyl)](Cl-2)SbF6 1a and 1b catalyze aldol reactions with ethyl glyoxylate with enantioselectivities ranging from 90 to 99% ee and syn reaction diastereoselections ranging from 90:10 to 95:5.

引用

页码：3375 / 3378

页数：4

共 8 条

[1] Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex
Evans, DA
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[2] Chiral copper(II) complexes as Lewis acids for catalyzed cycloaddition, carbonyl addition, and conjugate addition reactions
Evans, DA
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[J]. PURE AND APPLIED CHEMISTRY, 1999, 71 (08) : 1407 - 1415
[3] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde
Evans, DA
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Kozlowski, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) : 5814 - 5815
[4] C-2-symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters
Evans, DA
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10859 - 10860
[5] Cationic bis(oxazoline) and pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis acid catalysts. A comparative study in catalysis of Diels-Alder and aldol reactions
Evans, DA
Kozlowski, MC
Tedrow, JS
[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7481 - 7484
[6] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of enolsilanes to pyruvate esters
Evans, DA
Kozlowski, MC
Burgey, CS
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7893 - 7894
[7] ASYMMETRIC CATALYTIC ALDOL-TYPE REACTION WITH KETENE SILYL ACETALS - POSSIBLE INTERVENTION OF THE SILATROPIC ENE PATHWAY
MIKAMI, K
MATSUKAWA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) : 4077 - 4078
[8] Catalyzed enantioselective aldol additions of latent enolate equivalents
Nelson, SG
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (03) : 357 - 389

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