| Title | Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3H-Benzo[b]azepines and Axially Chiral Tetrasubstituted Allenes |
| Author | |
| Corresponding Author | Sun, Jianwei; Li, Pengfei |
| Publication Years | 2022-08-01
|
| DOI | |
| Source Title | |
| ISSN | 1523-7060
|
| EISSN | 1523-7052
|
| Abstract | Catalyst-controlled divergent reactions of 2,3-disubstituted indoles with propargylic alcohols were developed for the first time. In the presence of TsOH or B(C6F5)(3) as catalyst, 2,3-disubstituted indoles reacted smoothly with 3-alkynyl-3-hydroxyisoindolinones to afford 3H-benzo[b]azepines by selective C2(sp(2))-C3(sp(2)) ring expansion of indoles. In contrast, decreasing the catalyst strength (e.g., with chiral phosphoric acid) interrupted the cascade reactions, affording axially chiral tetrasubstituted allenes bearing an adjacent chiral quaternary carbon stereocenter. Control experiments provided insights into the reaction mechanism. |
| URL | [Source Record] |
| Indexed By | |
| Language | English
|
| Important Publications | NI Journal Papers
|
| SUSTech Authorship | Corresponding
|
| Funding Project | Shenzhen Innovation of Science and Technology Commission[20200925151614002]
; Guangdong Innovative Program[2019BT02Y335]
; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]
|
| WOS Research Area | Chemistry
|
| WOS Subject | Chemistry, Organic
|
| WOS Accession No | WOS:000850679400001
|
| Publisher | |
| ESI Research Field | CHEMISTRY
|
| Data Source | Web of Science
|
| Citation statistics |
Cited Times [WOS]:2
|
| Document Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/395910 |
| Department | Department of Chemistry 深圳格拉布斯研究院 |
| Affiliation | 1.Hong Kong Univ Sci & Technol, Dept Chem, Hong Kong, Peoples R China 2.Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Coll Sci, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China |
| First Author Affilication | Department of Chemistry; Shenzhen Grubbs Institute |
| Corresponding Author Affilication | Department of Chemistry; Shenzhen Grubbs Institute |
| Recommended Citation GB/T 7714 |
Qian, Chenxiao,Huang, Tingting,Sun, Jianwei,et al. Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3H-Benzo[b]azepines and Axially Chiral Tetrasubstituted Allenes[J]. ORGANIC LETTERS,2022.
|
| APA |
Qian, Chenxiao,Huang, Tingting,Sun, Jianwei,&Li, Pengfei.(2022).Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3H-Benzo[b]azepines and Axially Chiral Tetrasubstituted Allenes.ORGANIC LETTERS.
|
| MLA |
Qian, Chenxiao,et al."Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3H-Benzo[b]azepines and Axially Chiral Tetrasubstituted Allenes".ORGANIC LETTERS (2022).
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