N-Prolinylanthranilamide Pseudopeptides as Bifunctional Organocatalysts for Asymmetric Aldol Reactions

被引：46

作者：

Pearson, Anthony J. ^{[1
]}

Panda, Santanu ^{[1
]}

机构：

[1] Case Western Reserve Univ, Dept Chem, Cleveland, OH 44106 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 20期

关键词：

ENANTIOSELECTIVE SYNTHESIS; CATALYSTS; PROLINE; PEPTIDES; ISATINS; ACETONE; CONVOLUTAMYDINE; DERIVATIVES; KETONES; WATER;

D O I：

10.1021/ol202284n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Proline anthranilamide-based pseudopeptides were shown to be effective organocatalysts for enantioselective direct aldol reactions of a selection of aldehydes with various ketones with excellent yield, enantioselectivity up to 99% and anti to syn diastereoselectivity up to 25:1.

引用

页码：5548 / 5551

页数：4

共 33 条

[1] Water influences the enantioselectivity in the proline or prolinamide-catalyzed aldol addition of acetone to isatins [J].

Angelici, Gaetano ;

Correa, Rodrigo J. ;

Garden, Simon J. ;

Tomasini, Claudia .

TETRAHEDRON LETTERS, 2009, 50 (07) :814-817

[2]

[Anonymous], 2009, Curr. Bioact. Compd., DOI [10.2174/157340709787580900, DOI 10.2174/157340709787580900]

[3] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

[4] A DFT and AIM study of the proline-catalyzed asymmetric cross-aldol addition of acetone to isatins: A rationalization for the reversal of chirality [J].

Correa, Rodrigo J. ;

Garden, Simon J. ;

Angelici, Gaetano ;

Tomasini, Claudia .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (04) :736-744

[5] 2,4-Dinitrophenol as an Effective Cocatalyst: Greatly Improving the Activities and Enantioselectivities of Primary Amine Organocatalysts for Asymmetric Aldol Reactions [J].

Da, Chao-Shan ;

Che, Li-Ping ;

Guo, Qi-Peng ;

Wu, Feng-Chun ;

Ma, Xiao ;

Jia, Ya-Ning .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2541-2546

[6] Asymmetric catalysis mediated by synthetic peptides [J].

Davie, Elizabeth A. Colby ;

Mennen, Steven M. ;

Xu, Yingju ;

Miller, Scott J. .

CHEMICAL REVIEWS, 2007, 107 (12) :5759-5812

[7] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

[8] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents [J].

Galliford, Chris V. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8748-8758

[9] New Simple Hydrophobic Proline Derivatives as Highly Active and Stereoselective Catalysts for the Direct Asymmetric Aldol Reaction in Aqueous Medium [J].

Giacalone, Francesco ;

Gruttadauria, Michelangelo ;

Lo Meo, Paolo ;

Riela, Serena ;

Noto, Renato .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (17) :2747-2760

[10] Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxy-indolin-2-ones [J].

Guo, Qunsheng ;

Bhanushali, Mayur ;

Zhao, Cong-Gui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9460-9464

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