Organocatalytic Enantioselective Cycloaddition of o-Quinone Methides with Oxazolones: Asymmetric Synthesis of Dihydrocoumarins

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초록

The organocatalytic enantioselective cycloaddition of ortho-quinone methides with oxazolones promoted by a chiral binaphthyl-modified squaramide bifunctional organocatalyst was developed, allowing an efficient synthesis of chiral dihydrocoumarins with excellent enantioselectivity (up to 97 % ee). This approach represents a practical method for the preparation of chiral 3,4-dihydrocoumarin derivatives.

키워드

Organocatalysis; Cycloaddition; ortho-Quinone methides; Dihydrocoumarins; Oxazolones; BETA-SUBSTITUTED TRYPTOPHANS; FRIEDEL-CRAFTS ALKYLATION; CONJUGATE ADDITION; MICHAEL ADDITION; KETO-ESTERS; ACCESS; NITROALKENES; ARYLATION; PHOSPHONATES; FLUORINATION
제목
Organocatalytic Enantioselective Cycloaddition of o-Quinone Methides with Oxazolones: Asymmetric Synthesis of Dihydrocoumarins
저자
Kim, Kyeong Seop; Jang, Jihoon; Kim, Dae Young
DOI
10.1002/slct.202003817
발행일
2020-11-13
유형
Article
저널명
ChemistrySelect
권
5
호
42
페이지
13259 ~ 13262