Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins
نویسندگان
چکیده
We report herein an enantioselective acyl transfer protocol via electrophile activation. The reaction cascade sequence encompasses dinuclear zinc-catalyzed asymmetric Michael addition, intramolecular cyclization, and retro-Claisen reaction, which leads to a step- atom-economic approach variety of protected cyclic tertiary α-hydroxyketones in good yields with excellent enantioselectivities (24 examples, 56%-82% yield, 1.5-13 dr 79%-96% ee). Besides, the large-scale synthesis further transformation products demonstrate effectiveness this method for organic synthesis.
منابع مشابه
Asymmetric Michael addition of α-fluoro-α-nitro esters to nitroolefins: towards synthesis of α-fluoro-α-substituted amino acids.
α-Fluoro-α-nitro esters were used as reaction partners in Michael addition to nitroalkenes, and the products were obtained in excellent chemical yields and with high enantioselectivities. Moreover, α-fluoro-α-amino ester with a quaternary α-carbon was prepared for the first time.
متن کاملOrganocatalytic asymmetric direct vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to nitroolefins.
The first organocatalytic enantioselective direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactam to nitroolefins is developed using cinchona alkaloids as the catalysts. Both product enantiomers are accessible with moderate to good enantioselectivity.
متن کاملOrganocatalytic asymmetric Michael addition of 1-acetylcyclohexene and 1-acetylcyclopentene to nitroolefins.
Enantioselective organocatalytic Michael addition reactions of 1-acetylcyclohexene, 1-acetylcyclopentene and 1-acetylcyclobutene to nitroolefins have been developed. This is the first report where an α-branched enone has been activated by an amine catalyst for the asymmetric Michael addition reaction to an electrophile. The Michael products have also been cyclized to bicyclic compounds.
متن کاملAsymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins: facile preparation of fluorinated amines and tetrahydropyrimidines.
An asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins was developed, and the products were obtained in good chemical yields and with high stereoselectivities. Highly functionalized adducts provided ready access to fluorinated amines and tetrahydropyrimidines in an optically enriched form.
متن کاملCatalytic asymmetric Michael addition with curcumin derivative.
Catalytic asymmetric Michael additions with curcumin derivatives were achieved by a new series of tertiary amine-thiourea organocatalysts to afford the Michael adducts in high yields and excellent enantioselectivities.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Chemical synthesis
سال: 2023
ISSN: ['2769-5247']
DOI: https://doi.org/10.20517/cs.2022.35