exo-Selective asymmetric Diels-Alder reaction catalyzed by diamine salts as organocatalysts

被引：105

作者：

Kano, Taichi ^{[1
]}

Tanaka, Youhei ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 13期

关键词：

D O I：

10.1021/ol060621i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel binaphthyl-based diamine (R)-2 was designed and synthesized. A protonic acid-(R)-2 salt catalyst has the advantage of exhibiting unprecedented high exo selectivity in the asymmetric Diels-Alder reaction of alpha,beta-unsaturated aldehydes. For instance, the reaction between cinnamaldehyde and cyclopentadiene in the presence of 12 mol % of binaphthyl-based diamine (R)-2 and 10 mol % of p-TsOH center dot H2O in alpha, alpha, alpha-trifluorotoluene at -20 degrees C gave the corresponding exo cycloadduct with 92% ee as a major diastereomer (exo/endo = 13/1).

引用

页码：2687 / 2689

页数：3

共 33 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] ASYMMETRIC-SYNTHESIS OF EXO-NORBORNANE-2-CARBOXYLIC ACIDS [J].

AVENOZA, A ;

BUENO, MP ;

CATIVIELA, C ;

MAYORAL, JA .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :343-346

[3]

BRADDOCK DC, 2003, SYNLETT, V1121

[4] Iminium ion catalysis:: Use of the α-effect in the acceleration of the Diels-Alder reaction [J].

Cavill, JL ;

Peters, JU ;

Tomkinson, NCO .

CHEMICAL COMMUNICATIONS, 2003, (06) :728-729

[5]

Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO

[6]

2-B

[7]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[8]

2-D

[9] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[10] An efficient catalyst for highly enantioselective exo-Diels-Alder reaction between alkenoyl-1,3-oxazolidin-2-ones and cyclopentadiene [J].

Desimoni, G ;

Faita, G ;

Guala, M ;

Pratelli, C .

TETRAHEDRON, 2002, 58 (15) :2929-2935

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