N-Heterocyclic Carbene-Catalyzed Double Michael Addition: Stereoselective Synthesis of Spirofluorenes and Multisubstituted Indanes

被引：17

作者：

Xing, Fen ^{[1
]}

Feng, Ze-Nan ^{[1
]}

Wang, Ying ^{[1
]}

Du, Guang-Fen ^{[1
]}

Gu, Cheng-Zhi ^{[1
]}

Dai, Bin ^{[1
]}

He, Lin ^{[1
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832000, Xinjiang Uygur, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 08期

基金：

中国国家自然科学基金;

关键词：

N-heterocyclic carbene; Bronsted base; double Michael addition; spirofluorene; indane; FORMAL 3+2 ANNULATION; INTRAMOLECULAR STETTER REACTION; SINGLE-ELECTRON TRANSFER; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; GAMMA-BUTYROLACTONES; BETA-LACTONES; TRANSESTERIFICATION/ACYLATION REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; NONCOVALENT ORGANOCATALYST;

D O I：

10.1002/adsc.201701269

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The strong Bronsted basic character of N-heterocyclic carbenes (NHCs) has been used to promote the cascade double Michael addition between fluorenes and dienones. Under catalyst loadings of 1-5mol% of NHC, fluorene reacts with divinyl ketones (DVKs) to afford anti-spirofluorene compounds in high yields. However, when benzenedi(enones) were employed as Michael acceptors in the presence of 10mol% of NHC, fluorene undergoes a different inter- and intramolecular cascade double Michael addition, providing multi-substituted indanes in high yields with excellent diastereoselectivity.

引用

页码：1704 / 1710

页数：7

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