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

Ling Meng; Heyang Liu; Zhenyang Lin; Jun Wang

doi:10.1021/acs.orglett.2c01922

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

Ling Meng, Heyang Liu, Zhenyang Lin^*, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

14 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	5890-5895
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	32
Early online date	4 Aug 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c01922
Publication status	Published - 19 Aug 2022

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c01922

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

abstract = "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. ",

author = "Ling Meng and Heyang Liu and Zhenyang Lin and Jun Wang",

note = "Funding Information: The authors gratefully acknowledge the Shenzhen Basic Research Program for Shenzhen Virtual University Park (2021Szvup132) and the Research Grants Council of Hong Kong (HKUST16300021) for financial support. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

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doi = "10.1021/acs.orglett.2c01922",

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T1 - Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates

AU - Meng, Ling

AU - Liu, Heyang

AU - Lin, Zhenyang

AU - Wang, Jun

N1 - Funding Information: The authors gratefully acknowledge the Shenzhen Basic Research Program for Shenzhen Virtual University Park (2021Szvup132) and the Research Grants Council of Hong Kong (HKUST16300021) for financial support. Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/8/19

Y1 - 2022/8/19

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.orglett.2c01922

DO - 10.1021/acs.orglett.2c01922

M3 - Journal article

SN - 1523-7060

VL - 24

SP - 5890

EP - 5895

JO - Organic Letters

JF - Organic Letters

IS - 32

ER -

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

Abstract

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