Chiral C2-symmetric CuII complexes as catalysts for enantioselective hetero-Diels-Alder reactions

被引：0

作者：

Evans, DA ^{[1
]}

Olhava, EJ ^{[1
]}

Johnson, JS ^{[1
]}

Janey, JM ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1998年 / 37卷 / 24期

关键词：

asymmetric catalysis; copper; cycloadditions; Lewis acids; synthetic methods;

D O I：

10.1002/(SICI)1521-3773(19981231)37:24<3372::AID-ANIE3372>3.0.CO;2-K

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Air-stable and recyclable, the Cu(II)- (bis)oxazoline complex 1 efficiently catalyzes diastereo- and enantioselective hetero-Diels-Alder reactions between β,γ-unsaturated α-keto acid derivatives 2 and vinyl ethers for the synthesis of substituted dihydropyrans 3 [Eq. (1)]. Results of the crystal structure analysis of 1 in combination with calculations on model compounds indicate the formation of a reactive intermediate through replacement of the two H2O ligands with a chelating substrate. X = OEt, N(OMe)Me; R = alkyl, aryl, alkoxy, thiobenzyl.

引用

页码：3372 / 3375

页数：4

共 50 条

[1] Highly enantioselective hetero-Diels-Alder reactions catalyzed by a C2-symmetric bis(sulfoximine) Copper(II) complex
Bolm, C
Simic, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) : 3830 - 3831
[2] Chiral C2-symmetric Cu(II) complex immobilized in ionic liquids:: A recoverable catalytic system for enantioselective hetero-Diels-Alder reaction
Shin, Yong Je
Yeom, Chang-Eun
Kim, Mi Jeong
Kim, B. Moon
[J]. SYNLETT, 2008, (01) : 89 - 93
[3] Chiral chromium(III) porphyrins as highly enantioselective catalysts for hetero-Diels-Alder reactions between aldehydes and dienes
Berkessel, A
Ertürk, E
Laporte, C
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) : 223 - 228
[4] Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels-Alder reactions
Furuno, H
Hayano, T
Kambara, T
Sugimoto, Y
Hanamoto, T
Tanaka, Y
Jin, YZ
Kagawa, T
Inanaga, J
[J]. TETRAHEDRON, 2003, 59 (52) : 10509 - 10523
[5] Asymmetric Hetero-Diels-Alder Reactions Catalyzed by Chiral Dirhodium (II) Complexes
Anada, Masahiro
Hashimoto, Shunichi
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2019, 77 (06) : 553 - 565
[6] Catalytic enantioselective hetero-Diels-Alder reactions of an azo compound
Kawasaki, Masanori
Yamamoto, Hisashi
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) : 16482 - 16483
[7] DIANANE-CrIII-salen complexes as highly enantioselective catalysts for hetero-Diels-Alder reactions of aldehydes with dienes
Berkessel, Albrecht
Vogl, Nadine
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (22) : 5029 - 5035
[8] Catalytic enantioselective hetero-Diels-Alder reactions of an azo compound
Kawasaki, Masanori
Yamamoto, Hisashi
[J]. Journal of the American Chemical Society, 2006, 128 (51): : 16482 - 16483
[9] ORGN 536-Intramolecular hetero-Diels-Alder reactions, domino Knoevenagel/hetero-Diels-Alder and Knoevenagel/hetero-Diels-Alder/elimination reactions
Gowravaram, Sabitha
Reddy, Venkata E.
Reddy, Srinivas Ch
Maruthi, Ch
Yadav, J. S.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[10] Asymmetric hetero-Diels-Alder reactions catalyzed by chiral (salen)chromium(III) complexes
Schaus, SE
Brånalt, J
Jacobsen, EN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02): : 403 - 405

← 1 2 3 4 5 →