Citation: Ke Zhang, Sheng Zuo, Pengyuan You, Tong Ru, Fen-Er Chen. 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[J]. Chinese Chemical Letters, ;2024, 35(6): 109157. doi: 10.1016/j.cclet.2023.109157 shu

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 ^{a, c, d} ,
Sheng Zuo ^{c, d} ,
Pengyuan You ^{c, d} ,
Tong Ru ^{c, d} ,
Fen-Er Chen ^{a, b, c, d, *,}

a.
Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, College of Pharmacy, Yanbian University, Yanji 133002, China
b.
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
c.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai 200433, China
d.
Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, China

frchen@fudan.edu.cn

Received Date: 17 August 2023
Revised Date: 21 September 2023
Accepted Date: 25 September 2023
Available Online: 27 September 2023

Figures(5)

A novel asymmetric [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate with pyrrolidone-derived enones has been achieved to produce the functionalized tetrahydropyran-fused spirocyclic scaffolds 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 construction of medical interesting β^2,2-amino acids and β-lactams. Preliminary mechanistic research was well conducted.
- Pyrrolidine-2,3-diones,
- 2-Methylidenetrimethylene carbonate,
- Asymmetric annulation,
- Spiroheterocycles,
- Allylic 1,3-strain
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