Asymmetric Cascade Annulation Based on Enantioselective Oxa-Diels-Alder Cycloaddition of in Situ Generated Isochrornenyliums by Cooperative Binary Catalysis of Pd(OAc)2 and (S)-Trip

被引：144

作者：

Yu, Shu-Yan ^{[1
]}

Zhang, Hao ^{[1
]}

Gao, Yang ^{[1
]}

Mo, Lei ^{[1
]}

Wang, Shaozhong ^{[1
]}

Yao, Zhu-Jun ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing Natl Lab Microstruct, Nanjing 210093, Jiangsu, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 30期

关键词：

CONTAINING CARBONYL YLIDES; PHOSPHORIC-ACID; METAL CATALYSIS; LEWIS-ACID; CYCLIZATION; BENZANNULATION; CONSTRUCTION; DERIVATIVES; ENYNALS; O-ALKYNYL(OXO)BENZENES;

D O I：

10.1021/ja405764p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric cascade annulation between 2-hydroxystyrenes and 2-alkynylbenaldehyes or 1-(2-alkynylphenyl)ketones has been established with good to excellent enantioselectivities (up to >99.5% ee), on the basis of an enantioselective oxa-Diels-Alder cycloaddition of in situ generated metallo-isochromenylium intermediates, by cooperative binary catalysis of Pd(OAc)(2) and (S)-Trip. The developed methodology is workable for a broad spectrum of substrates and shows great efficiency in establishing dense multiple chiral centers including quaternary carbons of variable bridged ring systems. The mechanism study suggests that (S)-Trip plays multiple roles in assembling the reactants and controlling the stereoselectivity.

引用

页码：11402 / 11407

页数：6

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