首页|Palladium-catalyzed stereoselective decarboxylative[4+2]cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones:Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones

Palladium-catalyzed stereoselective decarboxylative[4+2]cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones:Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones

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A novel asymmetric[4+2]cycloaddition of 2-methylidenetrimethylene carbonate with pyrrolidone-derived enones has been achieved to produce the functionalized tetrahydropyran-fused spirocyclic scaf-folds via palladium-catalysis.An array of enantioenriched spiro-pyrrolidine-2,3-diones bearing adjacent quaternary and tertiary stereocenters are obtained in high yields with excellent enantioselectivities(up to 96%yield and 99%ee).The further transformation of the product has been accomplished for the con-struction of medical interesting β2,2-amino acids and β-lactams.Preliminary mechanistic research was well conducted.

Pyrrolidine-2,3-diones2-Methylidenetrimethylene carbonateAsymmetric annulationSpiroheterocyclesAllylic 1,3-strain

Ke Zhang、Sheng Zuo、Pengyuan You、Tong Ru、Fen-Er Chen

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Key Laboratory of Natural Medicines of the Changbai Mountain,Ministry of Education,College of Pharmacy,Yanbian University,Yanji 133002,China

Engineering Center of Catalysis and Synthesis for Chiral Molecules,Fudan University,Shanghai 200433,China

Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs,Shanghai 200433,China

College of Chemistry and Chemical Engineering,Jiangxi Normal University,Nanchang 330022,China

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National Key Research and Development Program of China

2021YFF0600704

2024

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
年,卷(期):2024.35(6)