Enantioselective Organocatalytic anti-Mannich-Type Reaction of N-Unprotected 3-Substituted 2-Oxindoles with Aromatic N-Ts-aldimines

被引：112

作者：

Cheng, Liang ^{[1
,2
]}

Liu, Li ^{[1
]}

Jia, Han ^{[1
]}

Wang, Dong ^{[1
]}

Chen, Yong-Jun ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 12期

基金：

中国国家自然科学基金;

关键词：

SUBSTITUTED ALPHA-CYANOACETATES; FRIEDEL-CRAFTS ALKYLATION; QUATERNARY STEREOCENTERS; CINCHONA ALKALOIDS; CONJUGATE ADDITION; NONADJACENT STEREOCENTERS; OXINDOLE ALKALOIDS; UNCARIA-TOMENTOSA; HILLMAN REACTION; ACYL IMINES;

D O I：

10.1021/jo9006688

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon centers in yields up to 90% with excellent diastereoselectivities (antil syn up to 95:5) and good enantioselectivies (up to 89% ee). A transition model for the anti-diastereo- and enantioselectivity of the reaction was proposed.

引用

页码：4650 / 4653

页数：4

共 40 条

[1] Highly diastereoselective synthesis of arylglycine derivatives via TFA-promoted Friedel-Crafts reactions of phenols with cyclic glyoxylate imines [J].

Chen, YJ ;

Lei, F ;

Liu, L ;

Wang, D .

TETRAHEDRON, 2003, 59 (38) :7609-7614

[2] Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives [J].

Cheng, Liang ;

Liu, Li ;

Sui, Yong ;

Wang, Dong ;

Chen, Yong-Jun .

TETRAHEDRON-ASYMMETRY, 2007, 18 (15) :1833-1843

[3]

Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858

[4] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[5]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[6]

2-V

[7] Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1996, 52 (39) :12651-12666

[8] Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues [J].

Edmondson, S ;

Danishefsky, SJ ;

Sepp-Lorenzino, L ;

Rosen, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2147-2155

[9] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[10] Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst [J].

Herrera, RP ;

Sgarzani, V ;

Bernardi, L ;

Ricci, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) :6576-6579

← 1 2 3 4 →