Nickel-Hydride-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes

Qingqin Huang; Ya Chen; Xueting Zhou; Lei Dai; Yixin Lu

doi:10.1002/anie.202210560

Nickel-Hydride-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes

Angew Chem Int Ed Engl. 2022 Nov 14;61(46):e202210560. doi: 10.1002/anie.202210560. Epub 2022 Oct 13.

Authors

Qingqin Huang^{1

2}, Ya Chen², Xueting Zhou^{1

2}, Lei Dai², Yixin Lu^{1

2}

Affiliations

¹ Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, Fujian, 350207, China.
² Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.

PMID: 36124410
DOI: 10.1002/anie.202210560

Abstract

Cyclopropanes are structural motifs that are widely present in natural products and bioactive molecules, and they are also tremendously useful building blocks in synthetic organic chemistry. Asymmetric synthesis of cyclopropane derivatives has been an intensively researched area over the years, but efficient asymmetric preparation of alkylcyclopropane scaffolds remains a challenging topic. Herein, we report a nickel-hydride-catalyzed enantioselective and diastereoselective hydroalkylation of cyclopropenes for facile synthesis of chiral alkylcyclopropane motifs. The reported method is efficient and versatile, taking place under mild reaction conditions, and having broad applicability and excellent functional group tolerance.

Keywords: Cyclopropanes; Cyclopropenes; Hydroalkylation; Nickel-Hydride.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Nickel* / chemistry
Stereoisomerism

Substances

cyclopropene
Nickel