Catalytic Asymmetric Intramolecular Bromolactonization of α,β-Unsaturated Ketones

Shenghui Liu; Hailong He; Min Gan; Peng Yi; Xiaojian Jiang

doi:10.1055/s-0037-1611860

Synlett, Table of Contents

Synlett 2019; 30(12): 1474-1478
DOI: 10.1055/s-0037-1611860

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Catalytic Asymmetric Intramolecular Bromolactonization of α,β-Unsaturated Ketones

Shenghui Liu

^aInternational Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China Email: chemjxj2015@jnu.edu.cn

,

Hailong He

^bGuangzhou Wanglaoji Pharmaceutical Company Limited, Guangzhou 510450, P. R. of China

,

Min Gan

^aInternational Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China Email: chemjxj2015@jnu.edu.cn

,

Peng Yi

^aInternational Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China Email: chemjxj2015@jnu.edu.cn

,

Xiaojian Jiang *

^aInternational Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China Email: chemjxj2015@jnu.edu.cn

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Abstract

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Abstract

Enantioselective bromolactonization by using an amino-urea catalyst to generate the important bromo-containing 3,4-dihydroisocoumarins is described. Excellent yields and good enantioselectivities could be achieved for various 3,4-dihydroisocoumarin compounds.

Key words

3,4-dihydroisocoumarins - bromolactonization - organocatalyst - enantioselectivity - deactivated olefins

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References

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13 The details are presented in the Supporting Information. CCDC 1911858 contains supplementary crystallographic data for compound 4b. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
14 General Procedure for Bromolactonization. To a PhMe/CHCl₃ (4 mL/1 ml) solution of α,β-unsaturated ketone (0.1 mmol, 1.0 equiv) and catalyst (7.1 mg, 0.15 mmol, 0.15 equiv) at 15°C, in dark under nitrogen was added halogen source (0.13 mmol, 1.3 equiv). The resulting mixture was stirred at 15°C and monitored by TLC. The reaction was quenched with saturated Na₂SO₃ (1 mL) at 15oC and then was warm to room temperature. The solution was diluted with water (3 mL) and extrated with EtOAc, dried over MgSO₄ and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc=3:1) to yield the corresponding lactone. Supporting Information provides full details and graphical guide.

Supplementary Material

Supporting Information