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

被引：19
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
收藏
页码：1704 / 1710
页数：7
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