南方科技大学知识苑(SUSTech KC): Unusual Enantiodivergence in Chiral Bronsted Acid-Catalyzed Asymmetric Allylation with beta-Alkenyl Allylic Boronates

题名	Unusual Enantiodivergence in Chiral Bronsted Acid-Catalyzed Asymmetric Allylation with beta-Alkenyl Allylic Boronates
作者	Gao, Shang 1,2; Duan, Meng3,4,5 ; Andreola, Laura R.6; Yu, Peiyuan4,5 ; Wheeler, Steven E.6; Houk, Kendall N.3; Chen, Ming 1
通讯作者	Houk, Kendall N.; Chen, Ming
发表日期	2022-09-01
DOI	10.1002/anie.202208908
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 影响因子和分区
ISSN	1433-7851
EISSN	1521-3773
摘要	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.
关键词	Boronates C-H center dot center dot center dot pi Interactions Chiral Phosphoric Acids Enantiodivergence Organocatalysis
相关链接	[来源记录]
收录类别	SCI
语种	英语
重要成果	NI论文
学校署名	其他
资助项目	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研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000850314900001
出版者	WILEY-V C H VERLAG GMBH
ESI学科分类	CHEMISTRY
来源库	Web of Science
引用统计	被引频次[WOS]：11
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/401494
专题	理学院_化学系深圳格拉布斯研究院
作者单位	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
推荐引用方式 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).