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

Authors
Kim, Yong HwanJang, SubinKim, Dae Young
Issue Date
Oct-2018
Publisher
대한화학회
Keywords
2-Hydroxy-1,4-naphthoquinones; 2-Nitroallylic acetates; Pyranonaphthoquinone; Organocatalysis
Citation
Bulletin of the Korean Chemical Society, v.39, no.10, pp 1160 - 1164
Pages
5
Journal Title
Bulletin of the Korean Chemical Society
Volume
39
Number
10
Start Page
1160
End Page
1164
URI
https://scholarworks.bwise.kr/sch/handle/2021.sw.sch/5608
DOI
10.1002/bkcs.11566
ISSN
0253-2964
1229-5949
Abstract
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.
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