Merging Manganese and Iminium Catalysis: Selective Hydroalkenylation of Unsaturated Aldehydes and Ketones

Author:

Zhao Chuan‐Gang1,Du Chaoyu1,Guo Zhenyu1,Li Weipeng1,Han Jie1,Xie Jin1ORCID

Affiliation:

1. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering Nanjing University Nanjing 210023 China

Abstract

AbstractThe use of synergistic catalytic strategy can usually circumvent the intrinsic limitations of one catalytic system. In this communication, we disclose a cooperative catalysis strategy of manganese and iminium catalysis to realize selective hydroalkenylation of unsaturated aldehydes and ketones. Its success stems from the LUMO activation of unsaturated carbonyl compounds with secondary amines as the organocatalyst and the synergistic HOMO activation of alkenylboronic acids with Mn2(CO)8Br2. This protocol exhibits several synthetic advances, e.g., simple operation, good functional group compatibility and good regioselectivity. The theoretical calculation indicates the migratory insertion followed by demetallation‐isomerization process is kinetically more favorable than Michael‐like nucleophilic addition. The use of proline‐derived organocatalyst can deliver the desired products in moderate enantioselectivity.

Funder

Key Technologies Research and Development Program

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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