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Enantioselective Decarboxylative Alkylation of β-Keto Acids to ortho-Quinone Methides as Reactive Intermediates: Asymmetric Synthesis of 2,4-Diaryl-1-benzopyrans

Hyun Jung Jeong and Dae Young Kim*

*Department of Chemistry, Soonchunhyang University, Asan, Chungnam 31538, Republic of Korea, Email: dyoungsch.ac.kr

H. J. Jeong, D. Y. Kim, Org. Lett., 2018, 20, 2944-2947.

DOI: 10.1021/acs.orglett.8b00993 (free Supporting Information)


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Abstract

An enantioselective decarboxylative alkylation of β-keto acids, followed by sequential cyclization and dehydration, enables an efficient asymmetric synthesis of  useful 2,4-diaryl-1-benzopyrans in good yields and high enantioselectivities . This one-pot, two-step sequence offers a facile way to prepare chiral 2,4-diaryl-1-benzopyran derivatives and tolerates a wide range of functional groups.

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Key Words

4H-chromenes, organocatalysis


ID: J54-Y2018