Aqueous enantioselective organocatalytic Diels-Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration

被引：117

作者：

Lemay, M ^{[1
]}

Ogilvie, WW ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol051476w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic hydrazides function as asymmetric organocatalysts in aqueous Diels-Alder reactions. The hydrazide is employed as the catalytic machinery in a compact camphor-derived framework that imparts facial selectivity to the cycloadditions. Kinetic evidence suggests the reaction involves rapid iminium formation.

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页码：4141 / 4144

页数：4

相关论文

共 32 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] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].

Austin, JF ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173

[3] Planar chiral PHANOLs as double hydrogen bonding donor organocatalysts: Synthesis and catalysis [J].

Braddock, DC ;

MacGilp, ID ;

Perry, BG .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1117-1130

[4] Planar chiral PHANOLs as organocatalysts for the Diels-Alder reaction via double hydrogen-bonding to a carbonyl group [J].

Braddock, DC ;

MacGilp, ID ;

Perry, BG .

SYNLETT, 2003, (08) :1121-1124

[5] 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

[6]

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

[7]

2-D

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

Dalko, PI ;

Moisan, L .

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

[9]

Fleming I., 1976, FRONTEIR ORBITALS OR

[10] Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].

France, S ;

Guerin, DJ ;

Miller, SJ ;

Lectka, T .

CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012

← 1 2 3 4 →