A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters

被引：12

作者：

Murauski, Kathleen J. R. ^{[1
]}

Walden, Daniel M. ^{[2
]}

Cheong, Paul Ha-Yeon ^{[2
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, 2145 Sheridan Rd, Evanston, IL 60208 USA

[2] Oregon State Univ, Dept Chem, 153 Gilbert Hall, Corvallis, OR USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 21期

关键词：

N-heterocyclic carbene; NHC; ternary catalysis; lactone; cooperative catalysis; Umpolung; homoenolate; N-HETEROCYCLIC CARBENE; HYDROGEN-BOND DONORS; CONJUGATE UMPOLUNG; GAMMA-BUTYROLACTONES; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CARBON ACTIVATION; TERTIARY-AMINES; DUAL CATALYSIS;

D O I：

10.1002/adsc.201701015

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A general and enantioselective N-heterocyclic carbene (NHC)-catalyzed lactonization of simple enals and alpha-ketoesters has been discovered using a new ternary cooperative catalytic system. The highly selective annulation was achieved by using a combination of a chiral NHC, a hydrogen-bond donor, and a metal salt, facilitating self-assembly of the reactive partners. A proposed model for this new mode of NHC chiral relay catalysis is supported by experimental and computational mechanistic studies.

引用

页码：3713 / 3719

页数：7

共 50 条

[21] Organocatalytic Asymmetric α-Functionalization of β-Ketoesters
Fang Ling
Shi Yan
Zhu Chengjian
[J]. PROGRESS IN CHEMISTRY, 2010, 22 (09) : 1679 - 1686
[22] Allenes in asymmetric catalysis: Rhodium(I)-catalyzed enantioselective addition of arylboronic acids to a-ketoesters
Cai, Feng
Pu, Xiaotao
Qi, Xiangbin
Antczak, Monika I.
Ready, Joseph M.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[23] Enantioselective Dearomative Cyclization Enabled by Asymmetric Cooperative Gold Catalysis
Zhao, Ke
Kohnke, Philip
Yang, Ziguang
Cheng, Xinpeng
You, Shu-Li
Zhang, Liming
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (37)
[24] Tertiary amine-Lewis acid cooperative asymmetric catalysis
Dixon, Darren J.
Sladojevich, Filippo
Yang, Ting
Ferrali, Alessandro
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[25] ORGN 292-Cooperative asymmetric catalysis with cinchona alkaloids
Deng, Li
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[26] Asymmetric Alkynylation of Imines by Cooperative Hydrogen Bonding and Metal Catalysis
de Armas, Pedro
Tejedor, David
Garcia-Tellado, Fernando
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (06) : 1013 - 1016
[27] Bifunctional asymmetric catalysis: Cooperative lewis acid/base systems
Paull, Daniel H.
Abraham, Ciby J.
Scerba, Michael T.
Alden-Danforth, Ethan
Lectka, Thomas
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (05) : 655 - 663
[28] Asymmetric Gold-Catalyzed Lactonizations in Water at Room Temperature
Handa, Sachin
Lippincott, Daniel J.
Aue, Donald H.
Lipshutz, Bruce H.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10658 - 10662
[29] Asymmetric alkylation of beta-ketoesters
Trost, BM
Radinov, R
Grenzer, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7879 - 7880
[30] Towards an asymmetric organocatallytic α-cyanation of β-ketoesters
Chowdhury, Raghunath
Schoergenhumer, Johannes
Novacek, Johanna
Waser, Mario
[J]. TETRAHEDRON LETTERS, 2015, 56 (14) : 1911 - 1914

← 1 2 3 4 5 →