Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid

被引：97

作者：

Akiyama, Takahiko ^{[1
]}

Honma, Yasuhiro ^{[1
]}

Itoh, Junji ^{[1
]}

Fuchibe, Kohei ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 03期

关键词：

addition to imines; amines; asymmetric catalysis; asymmetric synthesis; C-C bond formation; organic catalysis;

D O I：

10.1002/adsc.200700521

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

2-Trimethylsiloxyfuran underwent a vinylogous Mannich-type reaction with aldimines under the action of a new chiral phosphoric acid, bearing iodine on the 6,6'-positions of the binaphthyl group, as a chiral Bronsted acid to give gamma-butenolide derivatives bearing an amino functionality with high diastereo- and enantioselectivity.

引用

页码：399 / 402

页数：4

共 49 条

[1] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity [J].

Akiyama, T ;

Tamura, Y ;

Itoh, J ;

Morita, H ;

Fuchibe, K .

SYNLETT, 2006, (01) :141-143

[2] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].

Akiyama, T ;

Saitoh, Y ;

Morita, H ;

Fuchibe, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526

[3] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].

Akiyama, T ;

Morita, H ;

Itoh, J ;

Fuchibe, K .

ORGANIC LETTERS, 2005, 7 (13) :2583-2585

[4] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[5]

Akiyama T., 2004, ANGEW CHEM, V116, P1592, DOI DOI 10.1002/ANGE.200353240

[6] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[7] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[8] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[9]

[Anonymous], 2006, ANGEW CHEM, V118, P1550

[10]

[Anonymous], 2002, MACROMOL CHEM PHYS

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