Asymmetric [3+2] annulations catalyzed by a planar-chiral derivative of DMAP

被引：68

作者：

Bappert, Erhard ^{[1
]}

Muller, Peter ^{[1
]}

Fu, Gregory C. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 24期

关键词：

D O I：

10.1039/b603172b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A planar-chiral DMAP derivative catalyzes an intriguing [ 3 + 2] annulation reaction of silylated indenes to produce diquinanes that bear three contiguous stereocenters ( one quaternary and two tertiary).

引用

页码：2604 / 2606

页数：3

共 15 条

[1]

Arai S, 2001, ANGEW CHEM INT EDIT, V40, P234, DOI 10.1002/1521-3773(20010105)40:1<234::AID-ANIE234>3.0.CO

[2]

2-K

[3] Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter [J].

Hills, ID ;

Fu, GC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3921-3924

[4] Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids [J].

Hodous, BL ;

Ruble, JC ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2637-2638

[5] Enantioselective Staudinger synthesis of β-lactams catalyzed by a planar-chiral nucleophile [J].

Hodous, BL ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1578-1579

[6] Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile [J].

Kawano, Y ;

Kaneko, N ;

Mukaiyama, T .

CHEMISTRY LETTERS, 2005, 34 (11) :1508-1509

[7] Catalytic asymmetric Staudinger reactions to form β-lactams:: An unanticipated dependence of diastereoselectivity on the choice of the nitrogen substituent [J].

Lee, EC ;

Hodous, BL ;

Bergin, E ;

Shih, C ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11586-11587

[8] Synthesis of polyquinane natural products: An update [J].

Mehta, G ;

Srikrishna, A .

CHEMICAL REVIEWS, 1997, 97 (03) :671-719

[9] Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: Dual activation of the electrophile and the nucleophile [J].

Mermerian, AH ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4050-4051

[10] Catalytic enantioselective construction of all-carbon quaternary stereocenters: Synthetic and mechanistic studies of the C-acylation of silyl ketene acetals [J].

Mermerian, AH ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (15) :5604-5607

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