Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions | Zendy

Prakash D. Chaudhari | Zendy; BorCherng Hong | Zendy; Chao-Lin Wen | Zendy; GeneHsiang Lee | Zendy

Open Access

Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions

Author(s) -

Prakash D. Chaudhari,

BorCherng Hong,

Chao-Lin Wen,

GeneHsiang Lee

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b03049

Subject(s) - stereocenter , michael reaction , enantioselective synthesis , squaramide , nitro , cascade reaction , domino , organocatalysis , chemistry , organic chemistry , stereochemistry , catalysis , alkyl

An enantioselective domino Michael-Michael reaction of nitroolefins and 2-nitro-3-arylacrylates has been established, which provided a series of spirocyclopentane oxindoles with four consecutive stereocenters including quaternary α-nitro esters with good yields (up to 73%) and excellent enantioselectivities (up to 97% ee). The reaction was realized and optimized with the aid of a chiral squaramide-amine catalyst. The structures of 11 products were confirmed by single-crystal X-ray diffraction analysis.

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