Chiral 2,3-Disubstituted Indolines from Indoles and Aldehydes by Organocatalyzed Tandem Synthesis Involving Reduction by Trichlorosilane

被引：29

作者：

Chen, Lin ^{[1
,2
]}

Wang, Chao ^{[1
]}

Zhou, Li ^{[1
]}

Sun, Jian ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 10期

基金：

中国国家自然科学基金;

关键词：

enantioselectivity; indolines; reduction; tandem reactions; trichlorosilane; CATALYZED ASYMMETRIC HYDROGENATION; HIGHLY ENANTIOSELECTIVE REDUCTION; AMINO ACID-DERIVATIVES; BETA-ENAMINO ESTERS; N-ARYL IMINES; LEWIS-BASE; DOMINO REACTIONS; KINETIC RESOLUTION; CASCADE REACTIONS; AROMATIC KETONES;

D O I：

10.1002/adsc.201301133

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The organocatalytic trichlorosilane reduction system has been successfully utilized to develop a multi-step tandem approach for the easy preparation of chiral 2-methyl-3-alkylindolines starting from simple 2-methylindoles and aldehydes. A broad range of chiral 2-methyl-3-alkylindoline products was obtained with high yields and enantioselectivities and excellent stereoselectivities by this approach.

引用

页码：2224 / 2230

页数：7

共 50 条

[1] Organocatalytic Domino Reactions [J].

Alba, Andrea-Nekane ;

Companyo, Xavier ;

Viciano, Monica ;

Rios, Ramon .

CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) :1432-1474

[2] Routes toward enantiopure 2-substituted indolines: an overview [J].

Anas, Saithalavi ;

Kagan, Henri B. .

TETRAHEDRON-ASYMMETRY, 2009, 20 (19) :2193-2199

[3]

[Anonymous], 2006, ANGEW CHEM INT ED, V45, P7134

[4]

[Anonymous], 2011, ANGEW CHEM INT ED, V50, P7304

[5]

[Anonymous], 2006, ANGEW CHEM INT ED, V45, P1432

[6]

[Anonymous], 2007, ANGEW CHEM INT ED, V46, P3722

[7]

[Anonymous], ANGEW CHEM

[8]

[Anonymous], 2007, ANGEW CHEM INT ED, V46, P1570

[9]

[Anonymous], ANGEW CHEM INT ED

[10] Kinetic resolutions of indolines by a nonenzymatic acylation catalyst [J].

Arp, Forrest O. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) :14264-14265

← 1 2 3 4 5 →