Dinuclear Zinc-Catalyzed Asymmetric Tandem Reaction of α-Hydroxy-1-indanone: Access to Spiro[1-indanone-5,2′-γ-ybutyrolactones]

被引：30

作者：

Liu, Meng-Meng ^{[1
]}

Yang, Xiao-Chao ^{[1
]}

Hua, Yuan-Zhao ^{[1
]}

Chang, Jun-Biao ^{[1
]}

Wang, Min-Can ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, 100 Sci Ave, Zhengzhou 450001, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

基金：

中国国家自然科学基金;

关键词：

N-HETEROCYCLIC CARBENE; METHYLENE-GAMMA-BUTYROLACTONES; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; CYCLOHEXENE OXIDE; BIYOUYANAGIN-A; CONSTRUCTION; COPOLYMERIZATION; STRATEGY; ACID;

D O I：

10.1021/acs.orglett.9b02658

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient method for the enantioselective build of spiro[1-indanone-5,2'-gamma-butyrolactones] has been developed through the tandem Michael/transesterification reaction of alpha-hydroxy-l-indanone and alpha,beta-unsaturated esters. A broad range of spiro(1-indanone-butyrolacones) with contiguous stereocenters have been synthesized with excellent stereoselectivities (up to >20:1 dr, up to >99% ee) under the catalysis of dinuclear zinc complex. Moreover, the reaction can be run on a gram scale without affecting its stereoselectivities. A possible mechanism is proposed.

引用

页码：7089 / 7093

页数：5

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