Enantioselective synthesis of indanone spiro-isochromanone derivatives via a dinuclear zinc-catalyzed Michael/transesterification tandem reaction

被引：16

作者：

Yang, Xiao-Chao ^{[1
,2
]}

Xu, Meng ^{[1
,2
]}

Wang, Jin-Bao ^{[1
,2
]}

Liu, Meng-Meng ^{[1
,2
]}

Mathey, Francois ^{[1
,2
]}

Hua, Yuan-Zhao ^{[1
,2
]}

Wang, Min-Can ^{[1
,2
]}

机构：

[1] Zhengzhou Univ, Coll Chem, 100 Sci Rd, Zhengzhou 450000, Henan, Peoples R China

[2] Zhengzhou Univ, Inst Green Catalysis, 100 Sci Rd, Zhengzhou 450000, Henan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 20期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS ALKYLATION; MANNICH-TYPE REACTION; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALPHA-HYDROXYKETONES; CARBOXYLIC-ACIDS; MICHAEL REACTION; COPOLYMERIZATION; ISOCOUMARINS; STRATEGY;

D O I：

10.1039/d0ob00541j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective Michael/transesterification tandem reaction of alpha-hydroxy indanones with ortho-ester chalcones was realized using dinuclear zinc catalysts. A series of enantiomerically pure spiro[indanone-2,3 '-isochromane-1-one] derivatives were obtained in good yields with excellent stereoselectivities (up to >20 : 1 dr, up to >99% ee). This protocol could be conducted on a gram scale without affecting its stereoselectivities. In addition, the absolute stereochemistry of the products was determined by X-ray crystallographic analysis of 3ac, and a positive nonlinear effect was observed. Finally, a possible catalytic cycle was proposed to explain the origin of the enantioselectivity.

引用

收藏

页码：3917 / 3926

页数：10

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