Three‐Component Allylic Alkylation Reaction of α‐Diazo Ketones with Water and Allyl Carbonates for Construction of Homoallylic Alcohols

Author:

Yin Liping1,Zhang Xinyi2,Wang Baofan34,He Mingjin4,Li Yi4,Wang Shaozhen1,Jing Tongfei4,Kang Zhenghui234ORCID

Affiliation:

1. AnHui Provincial Engineering Research Center for Dental Materials and Application Institute of Synthesis and Application of Medical Materials Department of Pharmacy Wannan Medical College Wuhu 241002 People's Republic of China

2. School of Pharmaceutical Sciences Southern Medical University Guangzhou 510006 People's Republic of China

3. School of Pharmaceutical Sciences Guangzhou University of Chinese Medicine Guangzhou 510006 People's Republic of China

4. Zhongshan Institute for Drug Discovery Shanghai Institute of Materia Medica Chinese Academy of Sciences Zhongshan 528400 People's Republic of China

Abstract

AbstractA three‐component allylic alkylation reaction of α‐diazo ketones, water and allyl carbonate under the cooperative catalysis of Rh2(OAc)4, Pd2(dba)3 and Brønsted acid was disclosed. This method provides an expeditious access to α‐keto homoallylic alcohols in good to high yields. Controlled experiments support that the transformations proceed through cross‐interception of two active intermediates Pd‐allyl species and enol intermediates derived from oxonium ylides. Moreover, synthetic transformations of the generated products enable the creation of motifs enriched with dense functional groups, underscoring their potential as valuable building blocks.

Funder

National Natural Science Foundation of China

China Postdoctoral Science Foundation

Publisher

Wiley

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