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

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...

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Bibliographic Details
Published inBulletin of the Korean Chemical Society Vol. 39; no. 10; pp. 1160 - 1164
Main Authors Kim, Yong Hwan, Jang, Subin, Kim, Dae Young
Format Journal Article
LanguageEnglish
Published Weinheim Wiley‐VCH Verlag GmbH & Co. KGaA 01.10.2018
Wiley
대한화학회
Subjects
2‐Hydroxy‐1,4‐naphthoquinones
2‐Nitroallylic acetates
Chemistry
Chemistry, Multidisciplinary
Organocatalysis
Physical Sciences
Pyranonaphthoquinone
Science & Technology
화학
2-HYDROXY-1,4-NAPHTHOQUINONE
BAYLIS-HILLMAN ACETATES
2-Hydroxy-1,4-naphthoquinones
BETA-KETOACIDS
FLUORINATION
1,3-DICARBONYLS
Pyranonaphthoquinone
Organocatalysis
NAPHTHOQUINONES
2-Nitroallylic acetates
TETRAHYDROQUINOLINES
CONSTRUCTION
NITROALKENES
CONJUGATE ADDITION
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Summary: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.
Bibliography:https://onlinelibrary.wiley.com/doi/abs/10.1002/bkcs.11566
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.11566