Organic Letters
Organic Letters
5 years ago

Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles

Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles
Kezhou Wang, Haiyong Zhu, Dan Li, Jie Wang, Linqing Wang, Rui Wang, Yuan Wang, Dongxu Yang, Pengxin Wang
A nickel-mediated asymmetric allylic alkylation reaction between imidazole-modified ketones and nitroallylic acetates is presented. This reaction is catalyzed by a simple chiral diamine-nickel catalyst under mild conditions and leads to a series of novel enantioenriched α-allylic adducts in moderate to good yields with excellent enantioselectivities. Furthermore, transformation of the allylic adducts could smoothly lead to chiral γ-nitro-esters containing three continuous stereocenters in good yields.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02264

DOI: 10.1021/acs.orglett.7b02264

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