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

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초록

A novel and efficient asymmetric synthesis of 2,4-diaryl-1-benzopyrans via enantioselective decarboxylative alkylation of beta-keto acids to o-QM intermediates, followed by sequential cyclization and dehydration, has been developed. The synthetically useful chiral 2,4-diaryl-1-benzopyran derivatives were obtained in moderate to high yields and high enantioselectivities through a one-pot, two-step sequence. This approach offers a facile way to prepare chiral 2,4-diaryl-1-benzopyran derivatives with a wide range of functional group tolerance.

키워드

Enantioselective Decarboxylative Alkylation; β‑Keto Acids; ortho-Quinone Methides; Asymmetric Synthesis; 2; 4-Diaryl-1-benzopyrans; N-PHENYL TETRAHYDROISOQUINOLINE; OXIDATIVE COUPLING REACTION; CONJUGATE ADDITION; BRONSTED ACID; MICHAEL ADDITION; KETOACIDS; NITROALKENES; CYCLIZATION; CATALYSIS; ION
제목
Enantioselective Decarboxylative Alkylation of beta-Keto Acids to ortho-Quinone Methides as Reactive Intermediates: Asymmetric Synthesis of 2,4-Diaryl-1-benzopyrans
저자
Jeong, Hyun Jung; Kim, Dae Young
DOI
10.1021/acs.orglett.8b00993
발행일
2018-05-18
유형
Article
저널명
Organic Letters
권
20
호
10
페이지
2944 ~ 2947