Regioselective α-addition of vinylogous α-ketoester enolate in organocatalytic asymmetric Michael reactions: enantioselective synthesis of Rauhut-Currier type products

RSC Adv. 2022 Nov 9;12(49):32056-32060. doi: 10.1039/d2ra06416b. eCollection 2022 Nov 3.

ABSTRACT

Catalytic asymmetric α-regioselective Michael additions of vinylogous α-ketoester enolate are described herein. With 0.1-1.0 mol% loadings of a chiral bifunctional organocatalyst, the addition of a deconjugated α-keto ester to a series of nitroolefins, including the challenging β-alkylnitroalkenes, efficiently proceed, providing the Rauhut-Currier type products after isomerization of the terminal double bond in good yields (60-88%) with excellent regio- and enantioselectivities (94-99% ee, TON up to 160 with 0.5 mol% of the catalyst).

PMID:36415556 | PMC:PMC9644254 | DOI:10.1039/d2ra06416b

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