Organocatalytic peroxy-asymmetric allylic alkylation

被引：65

作者：

Feng, Xin ^{[1
]}

Yuan, Yu-Qing ^{[2
]}

Cui, Hai-Lei ^{[1
]}

Jiang, Kun ^{[1
]}

Chen, Ying-Chun ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China

[2] Third Hosp Chengdu, Chengdu, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 18期

基金：

中国国家自然科学基金;

关键词：

BAYLIS-HILLMAN REACTION; CHIRAL IONIC LIQUIDS; KINETIC RESOLUTION; ENANTIOSELECTIVE SYNTHESIS; GAMMA-BUTENOLIDES; CATALYZED BAYLIS; ALDOL REACTION; CONSTRUCTION; SUBSTITUTION; ACETATES;

D O I：

10.1039/b912110b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The peroxy-asymmetric allylic alkylation of hydroperoxyalkanes with Morita-Baylis-Hillman carbonates was catalysed by modified cinchona alkaloids (up to 93% ee), from which chiral alpha-methylene-beta-hydroxy esters could be efficiently derived.

引用

页码：3660 / 3662

页数：3

共 52 条

[1] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[2] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[3] The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry [J].

Basavaiah, Deevi ;

Rao, Kalapala Venkateswara ;

Reddy, Raju Jannapu .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1581-1588

[4] Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts [J].

Berkessel, Albrecht ;

Roland, Katrin ;

Neudoerfl, Jorg M. .

ORGANIC LETTERS, 2006, 8 (19) :4195-4198

[5] The asymmetric Baylis-Hillman reaction [J].

Brzezinski, LJ ;

Rafel, S ;

Leahy, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4317-4318

[6] Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates:: An organocatalytic allylic alkylation [J].

Cho, CW ;

Krische, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (48) :6689-6691

[7] Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates [J].

Cho, CW ;

Kong, JR ;

Krische, MJ .

ORGANIC LETTERS, 2004, 6 (08) :1337-1339

[8] Chemoselective Asymmetric N-Allylic Alkylation of Indoles with Morita-Baylis-Hillman Carbonates [J].

Cui, Hai-Lei ;

Feng, Xin ;

Peng, Jing ;

Lei, Jie ;

Jiang, Kun ;

Chen, Ying-Chun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5737-5740

[9] Dual Organocatalysis: Asymmetric Allylic-Allylic Alkylation of α,α-Dicyanoalkenes and Morita-Baylis-Hillman Carbonates [J].

Cui, Hai-Lei ;

Peng, Jing ;

Feng, Xin ;

Du, Wei ;

Jiang, Kun ;

Chen, Ying-Chun .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) :1574-1577

[10]

DLAIGH C, 2007, J ORG CHEM, V72, P7066

← 1 2 3 4 5 6 →