Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 11, Pages 2142-2147Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001570
Keywords
Amines; Michael addition; Asymmetric synthesis; Organocatalysis; Natural products
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Funding
- National Natural Science Foundation of China [20772110]
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A highly efficient organocatalytic synthesis of lapachol analogues from the Michael addition of naphthoquinone to various alpha,beta-unsaturated ketones catalyzed by primary amines is presented. Good to high yields (up to 93%) and high to excellent enantioselectivities (up to 98% ee) were obtained for the target compounds. MS (ESI) provided evidence for the key intermediates in the proposed mechanism.
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