The Use of Lewis Acids for Repairing Chemoselectivity of the Organocatalyzed Morita-Baylis-Hillman Reaction

被引：3

作者：

Fallek, Amit ^{[1
]}

Portnoy, Moshe ^{[1
]}

机构：

[1] Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-699678 Tel Aviv, Israel

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 11期

基金：

以色列科学基金会;

关键词：

Baylis-Hillman reaction; chemoselectivity; cooperative catalysis; Lewis acids; organocatalysis; synthetic methods; ACID/LEWIS BASE CATALYSIS; DIELS-ALDER REACTION; ALDOL REACTIONS; KETONES; SCAFFOLDS; ISATINS;

D O I：

10.1002/slct.201900157

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A substantial improvement in the chemoselectivity of the Morita-Baylis-Hillman reaction was realized by adding a diimino- or diaminopyridine coordination site within the backbone of bis-imidazole organocatalysts and using Lewis acids situated at this coordination site. The optimal outcome of 90-95% selectivity was achieved by proper matching of the catalyst/additive pair, as well as their respective amount (0.4 equiv. of AgOAc per 1 equiv. of diaminopyridine-incorporating catalyst).

引用

页码：3175 / 3179

页数：5

共 40 条

[1] Switching the Reactivity of Dihydrothiopyran-4-one with Aldehydes by Aqueous Organocatalysis: Baylis-Hillman, Aldol, or Aldol Condensation Reactions [J].

Abaee, M. Saeed ;

Mojtahedi, Mohammad M. ;

Pasha, Ghasem F. ;

Akbarzadeh, Elahe ;

Shockravi, Abbas ;

Mesbah, A. Wahid ;

Massa, Werner .

ORGANIC LETTERS, 2011, 13 (19) :5282-5285

[2] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].

Afewerki, Samson ;

Cordova, Armando .

CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570

[3] Advantages of polymer-supported multivalent organocatalysts for the Baylis-Hillman reaction over their soluble analogues [J].

Barak-Kulbak, Einav ;

Goren, Kerem ;

Portnoy, Moshe .

PURE AND APPLIED CHEMISTRY, 2014, 86 (11) :1805-1818

[4] Steric factors direct Baylis-Hillman and aldol reactions in titanium tetrachloride mediated coupling between α-keto esters and cyclohex-2-enone derivatives [J].

Basavaiah, D ;

Sreenivasulu, B ;

Rao, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) :5983-5991

[5] The Baylis-Hillman reaction: a novel concept for creativity in chemistry [J].

Basavaiah, Deevi ;

Veeraraghavaiah, Gorre .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :68-78

[6] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].

Basavaiah, Deevi ;

Reddy, Bhavanam Sekhara ;

Badsara, Satpal Singh .

CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674

[7] Highly efficient direct a larger-scale aldol reactions catalyzed by a flexible prolinamide based-metal Lewis acid bifunctional catalyst in the presence of water [J].

Chen, Guodong ;

Fu, Xiangkai ;

Li, Chao ;

Wu, Chuanlong ;

Miao, Qiang .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 702 :19-26

[8] Primary amine-metal Lewis acid bifunctional catalysts based on a simple bidentate ligand: direct asymmetric aldol reaction [J].

Daka, Philias ;

Xu, Zhenghu ;

Alexa, Alexandru ;

Wang, Hong .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :224-226

[9] Synergistic-cooperative combination of enamine catalysis with transition metal catalysis [J].

Deng, Yongming ;

Kumar, Siddhartha ;

Wang, Hong .

CHEMICAL COMMUNICATIONS, 2014, 50 (33) :4272-4284

[10] Pyridine-2,6-bis(oxazolines), helpful ligands for asymmetric catalysts [J].

Desimoni, G ;

Faita, G ;

Quadrelli, P .

CHEMICAL REVIEWS, 2003, 103 (08) :3119-3154

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