Highly Diastereo- and Enantioselective Organocatalyzed Michael/Oxa-Michael Sequence: Asymmetric Synthesis of Pyranonaphthoquinone Derivatives

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초록

An efficient asymmetric synthesis of pyranonaphthoquinones via Michael addition and oxo-Michael cyclization sequence of 2-hydroxy-1,4-naphthoquinone with (E)-2-nitroallylic acetates has been developed. The synthetically useful chiral pyranonaphthoquinone derivatives were obtained in moderate to high yields and high enantioselectivities. This approach offers a facile way to prepare chiral pyranonaphthoquinone derivatives with a wide range of functional group tolerance.

키워드

2-Hydroxy-1,4-naphthoquinones; 2-Nitroallylic acetates; Pyranonaphthoquinone; Organocatalysis; BAYLIS-HILLMAN ACETATES; CONJUGATE ADDITION; BETA-KETOACIDS; NITROALKENES; 2-HYDROXY-1,4-NAPHTHOQUINONE; TETRAHYDROQUINOLINES; CONSTRUCTION; NAPHTHOQUINONES; 1,3-DICARBONYLS; FLUORINATION
제목
Highly Diastereo- and Enantioselective Organocatalyzed Michael/Oxa-Michael Sequence: Asymmetric Synthesis of Pyranonaphthoquinone Derivatives
저자
Kim, Yong Hwan; Jang, Subin; Kim, Dae Young
DOI
10.1002/bkcs.11566
발행일
2018-10
유형
Article
저널명
Bulletin of the Korean Chemical Society
권
39
호
10
페이지
1160 ~ 1164