Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones

被引：20

作者：

Cong, Tiantian ^{[1
]}

Wang, Huamin ^{[1
]}

Li, Xiuzheng ^{[2
]}

Wu, Hai-Hong ^{[1
]}

Zhang, Junliang ^{[1
,3
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China

[2] Anhui Med Univ, Sch Pharm, 81 N Meishan Rd, Hefei 230032, Anhui, Peoples R China

[3] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 200438, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 62期

基金：

中国国家自然科学基金;

关键词：

SIMPLE INDOLE ALKALOIDS; DELTA-ACETOXY ALLENOATES; ASYMMETRIC-SYNTHESIS; DOMINO REACTION; PHOSPHINE CATALYSIS; 3+2 CYCLOADDITIONS; FACILE SYNTHESIS; SPIROOXINDOLES; ANNULATIONS; ALLENES;

D O I：

10.1039/c9cc04357h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones has been developed, which provides facile access to a series of optically enriched spiro[pyrrolidine-3,3 '-oxindole] compounds in good yields with good to excellent enantio- (up to 97% ee) and diastereoselectivities (up to 20 : 1 dr). Mechanistic studies indicate that this tandem reaction proceeds via an intermolecular aza-Michael/intramolecular Michael addition process.

引用

页码：9176 / 9179

页数：4

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