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Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles.
Org Biomol Chem. 2014 Oct 28; 12(40):8072-8.OB

Abstract

The first enantioselective aza-Morita–Baylis–Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent yields with up to 91% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhao X
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China. xinyanwu@ecust.edu.cn.
Li TZ
No affiliation info available
Qian JY
No affiliation info available
Sha F
No affiliation info available
Wu XY
No affiliation info available

MeSH

AcrylatesCrystallography, X-RayIminesIndolesModels, MolecularMolecular StructureNitrilesOxindolesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

25184554

Citation

Zhao, Xuan, et al. "Enantioselective aza-Morita-Baylis-Hillman Reaction Between Acrylates and N-Boc Isatin Ketimines: Asymmetric Construction of Chiral 3-substituted-3-aminooxindoles." Organic & Biomolecular Chemistry, vol. 12, no. 40, 2014, pp. 8072-8.
Zhao X, Li TZ, Qian JY, et al. Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles. Org Biomol Chem. 2014;12(40):8072-8.
Zhao, X., Li, T. Z., Qian, J. Y., Sha, F., & Wu, X. Y. (2014). Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles. Organic & Biomolecular Chemistry, 12(40), 8072-8. https://doi.org/10.1039/c4ob01358a
Zhao X, et al. Enantioselective aza-Morita-Baylis-Hillman Reaction Between Acrylates and N-Boc Isatin Ketimines: Asymmetric Construction of Chiral 3-substituted-3-aminooxindoles. Org Biomol Chem. 2014 Oct 28;12(40):8072-8. PubMed PMID: 25184554.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles. AU - Zhao,Xuan, AU - Li,Tian-Ze, AU - Qian,Jing-Ying, AU - Sha,Feng, AU - Wu,Xin-Yan, PY - 2014/9/4/entrez PY - 2014/9/4/pubmed PY - 2015/6/3/medline SP - 8072 EP - 8 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 12 IS - 40 N2 - The first enantioselective aza-Morita–Baylis–Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent yields with up to 91% ee. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/25184554/Enantioselective_aza_Morita_Baylis_Hillman_reaction_between_acrylates_and_N_Boc_isatin_ketimines:_asymmetric_construction_of_chiral_3_substituted_3_aminooxindoles_ DB - PRIME DP - Unbound Medicine ER -