Highly Diastereoselective Hydrosilane-Assisted Rhodium-Catalyzed Spiro-Type Cycloisomerization of Succinimide and Pyrazolone-Based Functional 1,6-Dienes

被引：10

作者：

Li, Hui-Lin ^{[1
,2
]}

Huang, Wei-Sheng ^{[1
,2
]}

Ling, Fang-Ying ^{[1
,2
]}

Li, Li ^{[1
,2
]}

Yan, Jun-Hao ^{[1
]}

Xu, Hao ^{[1
,2
]}

Xu, Li-Wen ^{[1
,2
,3
]}

机构：

[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Peoples R China

[2] Hangzhou Normal Univ, Lab Organosilicon Mat Technol Zhejiang Prov, Hangzhou 311121, Peoples R China

[3] Univ Chinese Acad Sci UCAS, State Key Lab Oxo Synth & Select Oxidat, Suzhou Res Inst SRI, Lanzhou Inst Chem Phys LICP, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2021年 / 16卷 / 13期

基金：

中国国家自然科学基金;

关键词：

rhodium; hydrosilane; diastereoselectivity; cycloisomerization reaction; 1; 6-dienes; C-BOND FORMATION; ASYMMETRIC-SYNTHESIS; CYCLIZATION; HYDROSILYLATION; ACID; EXO; SPIROPYRAZOLONES; PYRAZOL-5-ONES; HETEROCYCLES; ALKYLATION;

D O I：

10.1002/asia.202100372

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Organosilicon compounds are important reagents and synthetic intermediates that play a key role in the construction of new materials and complex products. Here we show a highly diastereoselective rhodium-catalyzed cycloisomerization of 1,6-dienes, in which the use of (EtO)(3)SiH accelerates the intramolecular cyclization reaction to afford a novel spiro-fused succinimide and pyrazolone derivatives in moderate to excellent yields as a single diastereoisomer. The proposed mechanism involves an active Rh-H species from the hydrosilane that is the H-donor in this spiro-type cycloisomerization reaction.

引用

页码：1730 / 1734

页数：5