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Maleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles.
Org Biomol Chem. 2015 May 28; 13(20):5629-35.OB

Abstract

A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kumar A
Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, India. sschimni@yahoo.com sschimni.chem@gndu.ac.in.
Sharma V
No affiliation info available
Kaur J
No affiliation info available
Kumar N
No affiliation info available
Chimni SS
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25747756

Citation

Kumar, Akshay, et al. "Maleimide as an Efficient Nucleophilic Partner in the aza-Morita-Baylis-Hillman Reaction: Synthesis of Chiral 3-substituted-3-aminooxindoles." Organic & Biomolecular Chemistry, vol. 13, no. 20, 2015, pp. 5629-35.
Kumar A, Sharma V, Kaur J, et al. Maleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles. Org Biomol Chem. 2015;13(20):5629-35.
Kumar, A., Sharma, V., Kaur, J., Kumar, N., & Chimni, S. S. (2015). Maleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles. Organic & Biomolecular Chemistry, 13(20), 5629-35. https://doi.org/10.1039/c5ob00182j
Kumar A, et al. Maleimide as an Efficient Nucleophilic Partner in the aza-Morita-Baylis-Hillman Reaction: Synthesis of Chiral 3-substituted-3-aminooxindoles. Org Biomol Chem. 2015 May 28;13(20):5629-35. PubMed PMID: 25747756.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Maleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles. AU - Kumar,Akshay, AU - Sharma,Vivek, AU - Kaur,Jasneet, AU - Kumar,Naveen, AU - Chimni,Swapandeep Singh, Y1 - 2015/03/09/ PY - 2015/3/10/entrez PY - 2015/3/10/pubmed PY - 2015/3/10/medline SP - 5629 EP - 35 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 20 N2 - A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/25747756/Maleimide_as_an_efficient_nucleophilic_partner_in_the_aza_Morita_Baylis_Hillman_reaction:_synthesis_of_chiral_3_substituted_3_aminooxindoles_ DB - PRIME DP - Unbound Medicine ER -