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Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol
Yang, J(杨洁)1; Zhang, Xiao-Ming1; Zhang, Fu-Min1; Wang, SH(王少华)2; Tu, Yong-Qiang1,3; Li, Zhen1; Wang, Xi-Chao1; Wang, Hong4
2020-05-25
Online publication date2020-03
Source PublicationAngewandte Chemie - International Edition   Impact Factor & Quartile Of Published Year  The Latest Impact Factor & Quartile
ISSN14337851
EISSN1521-3773
Volume59Issue:22Pages:8471-8475
page numbers5
AbstractAn enantioselective aldehyde α-alkylation/semipinacol rearrangement was achieved through organo-SOMO catalysis. The catalytically generated enamine radical cation serves as a carbon radical electrophile that can stereoselectively add to the alkene of an allylic alcohol and initiate ensuing ring-expansion of cyclopropanol or cyclobutanol. This tandem reaction enables the production of a wide range of nonracemic functionalizable α-quaternary-δ-carbonyl cycloketones in high yields and excellent enantioselectivity from simple aldehydes and allylic alcohols. As a key step, the intramolecular reaction was also successfully applied in the asymmetric total synthesis of (+)-cerapicol. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
KeywordAldehydes Alkylation Synthesis (chemical)Allylic alcohol Asymmetric total synthesis Enantioselective Intramolecular reactions Radical cations Ring expansion Tandem reaction Total synthesis
PublisherWiley-VCH Verlag
DOI10.1002/anie.202001100
Indexed ByEI ; SCIE ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000520253300001
EI Accession Number20201508395444
EI KeywordsEnantioselectivity
EI Classification Number801.4 Physical Chemistry ; 802.2 Chemical Reactions ; 804.1 Organic Compounds
Original Document TypeArticle
PMID 32124524
Citation statistics
Document Type期刊论文
Identifierhttps://ir.lzu.edu.cn/handle/262010/440469
Collection化学化工学院
兰州大学
药学院
Corresponding AuthorZhang, Xiao-Ming; Tu, Yong-Qiang
Affiliation
1.State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou; 730000, China;
2.School of Pharmacy, Lanzhou University, Lanzhou; 730000, China;
3.School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai; 200240, China;
4.School of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou; 310014, China
First Author AffilicationCollege of Chemistry and Chemical Engineering
Corresponding Author AffilicationCollege of Chemistry and Chemical Engineering
First Signature AffilicationCollege of Chemistry and Chemical Engineering
Recommended Citation
GB/T 7714
Yang, Jie,Zhang, Xiao-Ming,Zhang, Fu-Min,et al. Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol[J]. Angewandte Chemie - International Edition,2020,59(22):8471-8475.
APA Yang, Jie.,Zhang, Xiao-Ming.,Zhang, Fu-Min.,Wang, Shao-Hua.,Tu, Yong-Qiang.,...&Wang, Hong.(2020).Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol.Angewandte Chemie - International Edition,59(22),8471-8475.
MLA Yang, Jie,et al."Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol".Angewandte Chemie - International Edition 59.22(2020):8471-8475.
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