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Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes.
Org Lett. 2008 Jul 03; 10(13):2817-20.OL

Abstract

The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active functionalized naphthoquinones.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou WM
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, PRC.
Liu H
No affiliation info available
Du DM
No affiliation info available

MeSH

AlkenesCatalysisCinchona AlkaloidsCrystallography, X-RayHydroxylationModels, MolecularMolecular StructureNaphthoquinonesNitro CompoundsStereoisomerismThiourea

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18533672

Citation

Zhou, Wen-Ming, et al. "Organocatalytic Highly Enantioselective Michael Addition of 2-hydroxy-1,4-naphthoquinones to Nitroalkenes." Organic Letters, vol. 10, no. 13, 2008, pp. 2817-20.
Zhou WM, Liu H, Du DM. Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes. Org Lett. 2008;10(13):2817-20.
Zhou, W. M., Liu, H., & Du, D. M. (2008). Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes. Organic Letters, 10(13), 2817-20. https://doi.org/10.1021/ol800945e
Zhou WM, Liu H, Du DM. Organocatalytic Highly Enantioselective Michael Addition of 2-hydroxy-1,4-naphthoquinones to Nitroalkenes. Org Lett. 2008 Jul 3;10(13):2817-20. PubMed PMID: 18533672.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes. AU - Zhou,Wen-Ming, AU - Liu,Han, AU - Du,Da-Ming, Y1 - 2008/06/06/ PY - 2008/6/7/pubmed PY - 2008/9/17/medline PY - 2008/6/7/entrez SP - 2817 EP - 20 JF - Organic letters JO - Org Lett VL - 10 IS - 13 N2 - The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active functionalized naphthoquinones. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18533672/Organocatalytic_highly_enantioselective_Michael_addition_of_2_hydroxy_14_naphthoquinones_to_nitroalkenes_ L2 - https://doi.org/10.1021/ol800945e DB - PRIME DP - Unbound Medicine ER -