An Efficient Synthesis of Chiral Diamines with Rigid Backbones: Application in Enantioselective Michael Addition of Malonates to Nitroalkenes

被引：48

作者：

Zhu, Qiming ^{[1
,2
]}

Huang, Hanmin ^{[1
]}

Shi, Dengjian ^{[1
,2
]}

Shen, Zhiqiang ^{[1
]}

Xia, Chungu ^{[1
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 20期

基金：

中国国家自然科学基金;

关键词：

1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; STEREOSPECIFIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; MOTHER DIAMINE; ALDEHYDES; DIHYDROXYLATION; DERIVATIVES; CONVENIENT; MECHANISM;

D O I：

10.1021/ol901776n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient route for synthesis of enantiomerically pure biisoindoline and its isomer based on the diaza-Cope rearrangement reaction with chiral 1,2-bis(2-hydroxylphenyl)-1,2-diaminoethane as starting material has been developed. The newly prepared biisoindoline was employed as a chiral ligand in the NI(II)-catalyzed enantioselective Michael addition of malonates to conjugated nitroalkenes, and good to excellent enantioselectivities were obtained.

引用

收藏

页码：4536 / 4539

页数：4

相关论文

共 49 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[2]

Alexakis A, 2000, ANGEW CHEM INT EDIT, V39, P4093, DOI 10.1002/1521-3773(20001117)39:22<4093::AID-ANIE4093>3.0.CO

[3]

2-R

[4] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].

Andrey, O ;

Alexakis, A ;

Tomassini, A ;

Bernardinelli, G .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168

[5] Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin [J].

Andrey, O ;

Vidonne, A ;

Alexakis, A .

TETRAHEDRON LETTERS, 2003, 44 (43) :7901-7904

[6] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].

Andrey, O ;

Alexakis, A ;

Bernardinelli, G .

ORGANIC LETTERS, 2003, 5 (14) :2559-2561

[7] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].

Barnes, DM ;

Ji, JG ;

Fickes, MG ;

Fitzgerald, MA ;

King, SA ;

Morton, HE ;

Plagge, FA ;

Preskill, M ;

Wagaw, SH ;

Wittenberger, SJ ;

Zhang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105

[8] trans-1,2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition [J].

Bennani, YL ;

Hanessian, S .

CHEMICAL REVIEWS, 1997, 97 (08) :3161-3195

[9] [1,2-BIS(2-HYDROXYPHENYL)ETHYLENEDIAMINE]DICHLOROPLATINUM(II), A NEW COMPOUND FOR THE THERAPY OF OVARIAN-CANCER .2. SYNTHESIS AND PRELIMINARY TESTING OF THE ENANTIOMERIC COMPLEXES [J].

BERNHARDT, G ;

GUST, R ;

REILE, H ;

VOMORDE, HD ;

MULLER, R ;

KELLER, C ;

SPRUSS, T ;

SCHONENBERGER, H ;

BURGEMEISTER, T ;

MANNSCHRECK, A ;

RANGE, KJ ;

KLEMENT, U .

JOURNAL OF CANCER RESEARCH AND CLINICAL ONCOLOGY, 1992, 118 (03) :201-208

[10] Selective hydrogenation for fine chemicals: Recent trends and new developments [J].

Blaser, HU ;

Malan, C ;

Pugin, B ;

Spindler, F ;

Steiner, H ;

Studer, M .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151

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