3 years ago

Catalytically Enantioselective Synthesis of Acyclic α-Tertiary Amines through Desymmetrization of 2-Substituted 2-Nitro-1,3-diols

Catalytically Enantioselective Synthesis of Acyclic
α-Tertiary Amines through Desymmetrization of 2-Substituted
2-Nitro-1,3-diols
Shan-Shui Meng, Wen-Hua Zheng, Wu-Bang Tang
Highly enantioselective synthesis of acyclic α-tertiary amines through asymmetric desymmetrization is reported. This approach is based on chiral phosphoric acid mediated, enantioselective, oxidative desymmetrization of 2-substituted 2-nitro-1,3-diolbenzylidine acetals in the presence of DMDO as an oxidant. The method allows for the formation of a wide variety of chiral 2-nitro-1,3-diols in high enantioselectivity, which could be transformed into optically pure, unnatural α-alkyl series. The synthetic utility of this method has been further demonstrated by the expedient construction of the core structure of natural products manzacidins enantioselectively.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03581

DOI: 10.1021/acs.orglett.7b03581

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