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
收藏
页码：9176 / 9179
页数：4
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