Enantioselective Activation of Stable Carboxylate Esters as Enolate Equivalents via N-Heterocyclic Carbene Catalysts

被引：173

作者：

Hao, Lin ^{[1
]}

Du, Yu ^{[1
]}

Lv, Hui ^{[1
]}

Chen, Xingkuan ^{[1
]}

Jiang, Huishen ^{[1
]}

Shao, Yaling ^{[1
]}

Chi, Yonggui Robin ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 08期

基金：

新加坡国家研究基金会;

关键词：

DIELS-ALDER REACTIONS; ALPHA-FUNCTIONALIZED ALDEHYDES; INTERNAL REDOX REACTION; NUCLEOPHILIC CARBENES; ASYMMETRIC-SYNTHESIS; RING EXPANSION; TRANSESTERIFICATION/ACYLATION REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; CONJUGATE UMPOLUNG; ACID-DERIVATIVES;

D O I：

10.1021/ol300676w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first N-Heterocyclic Carbene (NHC) mediated activation of stable carboxylate esters to generate enolate intermediates is disclosed. The catalytically generated arylacetic ester enolates undergo enantioselective reactions with alpha,beta-unsaturated imines.

引用

页码：2154 / 2157

页数：4

共 80 条

[1] A Surprising Mechanistic "Switch" in Lewis Acid Activation: A Bifunctional, Asymmetric Approach to α-Hydroxy Acid Derivatives [J].

Abraham, Ciby J. ;

Paull, Daniel H. ;

Bekele, Tefsit ;

Scerba, Michael T. ;

Dudding, Travis ;

Lectka, Thomas .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :17085-17094

[2] Direct organocatalytic synthesis of enantiopure succinimides from β-lactam aldehydes through ring expansion promoted by azolium salt precatalysts [J].

Alcaide, Benito ;

Almendros, Pedro ;

Cabrero, Gema ;

Ruiz, M. Pilar .

CHEMICAL COMMUNICATIONS, 2007, (45) :4788-4790

[3] Fused polycyclic nucleophilic carbenes - synthesis, structure, and function [J].

Arduengo, Anthony J., III ;

Iconaru, Luigi I. .

DALTON TRANSACTIONS, 2009, (35) :6903-6914

[4] Catalytic, enantioselective [4+2]-cycloadditions of ketene enolates and o-quinones:: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives [J].

Bekele, T ;

Shah, MH ;

Wolfer, J ;

Abraham, CJ ;

Weatherwax, A ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1810-1811

[5] Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations [J].

Belmessieri, Dorine ;

Morrill, Louis C. ;

Simal, Carmen ;

Slawin, Alexandra M. Z. ;

Smith, Andrew D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) :2714-2720

[6] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].

Biju, Akkattu T. ;

Kuhl, Nadine ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195

[7] N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].

Bode, Jeffrey W. ;

Sohn, Stephanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+

[8] N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones [J].

Burstein, Christian ;

Tschan, Serena ;

Xie, Xiulan ;

Glorius, Frank .

SYNTHESIS-STUTTGART, 2006, (14) :2418-2439

[9] The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters [J].

Candish, Lisa ;

Lupton, David W. .

ORGANIC LETTERS, 2010, 12 (21) :4836-4839

[10]

Chiang P.-C., 2011, TCI MAIL, V149, P2

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