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


ABSTRACT: 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 ?-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.

SUBMITTER: Chaudhari PD 

PROVIDER: S-EPMC6648780 | BioStudies | 2019-01-01

REPOSITORIES: biostudies

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