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Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.
Org Biomol Chem. 2013 Mar 28; 11(12):1921-4.OB

Abstract

The asymmetric catalytic aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with MVK has been established by using chiral amino and phosphino catalysts. The reaction resulted in biomedically important 3-substituted 3-amino-2-oxindoles in good yields (>80% for most cases) and with excellent enantioselectivity (90-99% ee). Twenty-eight cases assembled with chiral quaternary stereogenic centers have been examined under convenient systems.

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Authors+Show Affiliations

Hu FL
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, PR China.
Wei Y
No affiliation info available
Shi M
No affiliation info available
Pindi S
No affiliation info available
Li G
No affiliation info available

MeSH

Aza CompoundsCatalysisIminesIndolesIsatinMolecular StructureNitrilesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23407608

Citation

Hu, Fang-Le, et al. "Asymmetric Catalytic aza-Morita-Baylis-Hillman Reaction for the Synthesis of 3-substituted-3-aminooxindoles With Chiral Quaternary Carbon Centers." Organic & Biomolecular Chemistry, vol. 11, no. 12, 2013, pp. 1921-4.
Hu FL, Wei Y, Shi M, et al. Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers. Org Biomol Chem. 2013;11(12):1921-4.
Hu, F. L., Wei, Y., Shi, M., Pindi, S., & Li, G. (2013). Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers. Organic & Biomolecular Chemistry, 11(12), 1921-4. https://doi.org/10.1039/c3ob27495k
Hu FL, et al. Asymmetric Catalytic aza-Morita-Baylis-Hillman Reaction for the Synthesis of 3-substituted-3-aminooxindoles With Chiral Quaternary Carbon Centers. Org Biomol Chem. 2013 Mar 28;11(12):1921-4. PubMed PMID: 23407608.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers. AU - Hu,Fang-Le, AU - Wei,Yin, AU - Shi,Min, AU - Pindi,Suresh, AU - Li,Guigen, Y1 - 2013/02/13/ PY - 2013/2/15/entrez PY - 2013/2/15/pubmed PY - 2014/3/19/medline SP - 1921 EP - 4 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 11 IS - 12 N2 - The asymmetric catalytic aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with MVK has been established by using chiral amino and phosphino catalysts. The reaction resulted in biomedically important 3-substituted 3-amino-2-oxindoles in good yields (>80% for most cases) and with excellent enantioselectivity (90-99% ee). Twenty-eight cases assembled with chiral quaternary stereogenic centers have been examined under convenient systems. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/23407608/Asymmetric_catalytic_aza_Morita_Baylis_Hillman_reaction_for_the_synthesis_of_3_substituted_3_aminooxindoles_with_chiral_quaternary_carbon_centers_ L2 - https://doi.org/10.1039/c3ob27495k DB - PRIME DP - Unbound Medicine ER -