Synlett 2019; 30(12): 1474-1478
DOI: 10.1055/s-0037-1611860
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Intramolecular Bromolactonization of α,β-Unsaturated Ketones

Shenghui Liu
a  International 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
b  Guangzhou Wanglaoji Pharmaceutical Company Limited, Guangzhou 510450, P. R. of China
,
Min Gan
a  International 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
a  International 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
,
a  International 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
› Author Affiliations
We thank the Natural Science Foundation of Guangdong Province (Grant No. 2017B050506006) and Fundamental Research Funds for the Central University (Grant No. 21617470) for financial support.
Further Information

Publication History

Received: 29 April 2019

Accepted after revision: 21 May 2019

Publication Date:
12 June 2019 (eFirst)

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.

Supporting Information

 
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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.