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
Ke Zhang 1Sheng Zuo 2Pengyuan You 2Tong Ru 2Fen-Er Chen3
作者信息
- 1. 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
- 2. 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
- 3. Key Laboratory of Natural Medicines of the Changbai Mountain,Ministry of Education,College of Pharmacy,Yanbian University,Yanji 133002,China;College of Chemistry and Chemical Engineering,Jiangxi Normal University,Nanchang 330022,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
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Abstract
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.
Key words
Pyrrolidine-2,3-diones/2-Methylidenetrimethylene carbonate/Asymmetric annulation/Spiroheterocycles/Allylic 1,3-strain引用本文复制引用
基金项目
National Key Research and Development Program of China(2021YFF0600704)
出版年
2024
NETL
NSTL
万方数据