Rhodium-Catalyzed Enantioselective Formal [4+1] Cycloaddition of Diazooxindoles and the Danishefsky Diene

被引：6

作者：

Cao, Fei ^{[1
]}

Hu, Fang ^{[1
]}

Xie, Qi-Mei ^{[1
]}

Luo, Gao-Ya ^{[1
]}

Chu, Wen-Dao ^{[1
]}

He, Long ^{[1
]}

Liu, Quan-Zhong ^{[1
]}

机构：

[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Coll Chem & Chem Engn, Nanchong 637000, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 02期

关键词：

cycloaddition; cyclopropanes; dienes; rhodium; spiro compounds; VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; THERMAL REARRANGEMENTS; DERIVATIVES; 1,4-DIPOLES; ESTERS; CORE;

D O I：

10.1002/ajoc.201700639

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically enriched cyclopentenones are synthetically versatile molecules, and their rapid and efficient straightforward assembly from simple starting materials is highly desired. Herein, we report a rhodium-catalyzed enantioselective formal [4+1] cycloaddition of diazooxindoles and the Danishefsky diene. The formation of cyclopentenones proceeds via ring expansion of the vinylcyclopropanes formed in situ via cyclopropanation. The optically and highly structurally enriched indoline spirocyclopentenone bearing an all-carbon stereocenter was formed in a one-pot, two-step manner in good to excellent yields and enantioselectivities (up to 90% ee).

引用

页码：363 / 366

页数：4

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