| Title | Unusual Enantiodivergence in Chiral Bronsted Acid-Catalyzed Asymmetric Allylation with beta-Alkenyl Allylic Boronates |
| Author | |
| Corresponding Author | Houk, Kendall N.; Chen, Ming |
| Publication Years | 2022-09-01
|
| DOI | |
| Source Title | |
| ISSN | 1433-7851
|
| EISSN | 1521-3773
|
| Abstract | We report herein a rare example of enantiodivergent aldehyde addition with beta-alkenyl allylic boronates via chiral Bronsted acid catalysis. 2,6-Di-9-anthracenyl-substituted chiral phosphoric acid-catalyzed asymmetric allylation using beta-vinyl substituted allylic boronate gave alcohols with R absolute configuration. The sense of asymmetric induction of the catalyst in these reactions is opposite to those in prior reports. Moreover, in the presence of the same acid catalyst, the reactions with beta-2-propenyl substituted allylic boronate generated homoallylic alcohol products with S absolute configuration. Unusual substrate-catalyst C-H center dot center dot center dot pi inter- actions in the favoured reaction transition state were identified as the origins of observed enantiodivergence through DFT computational studies. |
| Keywords | |
| URL | [Source Record] |
| Indexed By | |
| Language | English
|
| Important Publications | NI Journal Papers
|
| SUSTech Authorship | Others
|
| Funding Project | National Institute of Health[R35 GM147523-01]
; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]
; National Science Foundation (CAREER Award)["CHE-2042353","CHE-1764328"]
; National Science Foundation[OCI-1053575]
|
| WOS Research Area | Chemistry
|
| WOS Subject | Chemistry, Multidisciplinary
|
| WOS Accession No | WOS:000850314900001
|
| 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/401494 |
| Department | Department of Chemistry 深圳格拉布斯研究院 |
| Affiliation | 1.Auburn Univ, Dept Chem & Biochem, Auburn, AL 36849 USA 2.China Pharmaceut Univ, Nanjing 210009, Peoples R China 3.Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA 4.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China 5.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China 6.Univ Georgia, Dept Chem, Athens, GA 30602 USA |
| Recommended Citation GB/T 7714 |
Gao, Shang,Duan, Meng,Andreola, Laura R.,et al. Unusual Enantiodivergence in Chiral Bronsted Acid-Catalyzed Asymmetric Allylation with beta-Alkenyl Allylic Boronates[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022.
|
| APA |
Gao, Shang.,Duan, Meng.,Andreola, Laura R..,Yu, Peiyuan.,Wheeler, Steven E..,...&Chen, Ming.(2022).Unusual Enantiodivergence in Chiral Bronsted Acid-Catalyzed Asymmetric Allylation with beta-Alkenyl Allylic Boronates.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
|
| MLA |
Gao, Shang,et al."Unusual Enantiodivergence in Chiral Bronsted Acid-Catalyzed Asymmetric Allylation with beta-Alkenyl Allylic Boronates".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022).
|
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