Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates

Meng, Ling1,2,3,4; Liu, Heyang3; Lin, Zhenyang2; Wang, Jun1,4

2022-08-01

10.1021/acs.orglett.2c01922

ORGANIC LETTERS   Impact Factor & Quartile

1523-7060

1523-7052

Highly efficient and straightforward access to enantioenriched five-membered ring-fused chromanones is developed via [3+2]-cycloaddition of 3-cyanochromones with Morita- Baylis-Hillman carbonates. Densely functionalized chiral cyclopenta[b]chromanones with three continuous quaternary and tertiary stereogenic carbon centers were obtained in high yields with high ee and dr (<= 97% yield, 97% ee, and > 20:1 dr). Moreover, density functional theory calculations have been carried out to investigate the mechanism and regio-and diastereoselectivity of the reaction.

SCI

English

NI Journal Papers

Non-SUSTech

Shenzhen Basic Research Program for Shenzhen Virtual University Park[2021Szvup132] ; Research Grants Council of Hong Kong[HKUST16300021]

Chemistry

Chemistry, Organic

WOS:000838151000001

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Hong Kong Baptist Univ, Dept Chem, Hong Kong 999077, Peoples R China
2.Hong Kong Univ Sci & Technol, Dept Chem, Hong Kong 999077, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
4.Hong Kong Baptist Univ, Inst Res & Continuing Educ, Shenzhen 518000, Peoples R China

Meng, Ling,Liu, Heyang,Lin, Zhenyang,et al. Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates[J]. ORGANIC LETTERS,2022.

Meng, Ling,Liu, Heyang,Lin, Zhenyang,&Wang, Jun.(2022).Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates.ORGANIC LETTERS.

Meng, Ling,et al."Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates".ORGANIC LETTERS (2022).