Access to Enantioenriched Allylic Alcohols via Peptide-Mimic Phosphonium Salt-Catalyzed Asymmetric Aerobic Hydroxylation
Jixing Che
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
These authors contributed equally.
Search for more papers by this authorSiqiang Fang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Department of Chemistry, National University of Singapore, Science Drive 3, Singapore, 117543 Singapore
These authors contributed equally.
Search for more papers by this authorZanjiao Liu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorJiajia He
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorJia-Yan Zheng
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorFan Wang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorCorresponding Author
Tianli Wang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
E-mail: [email protected]Search for more papers by this authorJixing Che
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
These authors contributed equally.
Search for more papers by this authorSiqiang Fang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Department of Chemistry, National University of Singapore, Science Drive 3, Singapore, 117543 Singapore
These authors contributed equally.
Search for more papers by this authorZanjiao Liu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorJiajia He
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorJia-Yan Zheng
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorFan Wang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
Search for more papers by this authorCorresponding Author
Tianli Wang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, Sichuan, 610064 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
The development of catalytic asymmetric methods that enable access to value-added functionalities or structures, exemplified by allylic alcohols, is a highly interesting yet challenging topic from both academic and industrial perspectives. However, before recent advances in chemical catalysis, there were scarce protocols toward constructing enantioenriched tertiary allylic alcohol scaffolds. In this context, peptide-mimic phosphonium salts were found to be highly efficient in catalytic asymmetric α-hydroxylation of α,β-unsaturated and/or β,ϒ-unsaturated compounds with satisfactory regio- and stereochemical outcomes (up to 97% yield and 95% ee). This methodology tolerates a broad array of substrates and thus provides an expeditious and unified platform for the assembly of enantioenriched tertiary allylic alcohols by avoiding the use of additional reductants and expensive metal catalysts. Furthermore, the power of this protocol is enlarged by simple conditions and the use of air as a source of hydroxyl functionality.
Supporting Information
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Appendix S1: Supporting Information |
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