ENANTIOSELECTIVE SYNTHESIS OF 4,5-DISUBSTITUTED PYRROLIDIN-2-ONE DERIVATIVES WITH TWO STEREOCENTERS ON THE BASIS OF MICHAEL ADDUCTS

Natalija Orlova; Maxim Vorona; Vladislavs Baskevics; Marina Petrova; Sergey Belyakov; Helena Kazoka; Ruslan Muhamadejev; Grigory Veinberg

doi:10.1007/5586

ENANTIOSELECTIVE SYNTHESIS OF 4,5-DISUBSTITUTED PYRROLIDIN-2-ONE DERIVATIVES WITH TWO STEREOCENTERS ON THE BASIS OF MICHAEL ADDUCTS

Natalija Orlova, Maxim Vorona, Vladislavs Baskevics, Marina Petrova, Sergey Belyakov, Helena Kazoka, Ruslan Muhamadejev, Grigory Veinberg

Abstract

The addition of malonates to trans-β-alkyl-β-nitrostyrenes in the presence of chiral Mg²⁺ bisoxazoline complex and Ni²⁺ and Co²⁺ bis((S,S)- or (R,R)-N,N'-dibenzylcyclohexane-1,2-diamine) complexes resulted in the formation of Michael adducts with two stereocenters which were used as key precursors for the preparation of potentially biologically active enantiopure 4,5-disubstituted pyrrolidin-2-one derivatives.

Keywords

chiral Mg2+, Ni2+, and Co2+ complexes; 4,5-disubstituted pyrrolidin-2-ones; Michael adduct; asymmetric catalysis

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Supplementary File(s): Supporting information (7MB)

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv

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