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An organocatalytic Mannich/denitration reaction for the asymmetric synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: formal synthesis of AG-041R.
Chemistry. 2015 Mar 02; 21(10):3933-6.C

Abstract

The highly enantioselective organocatalytic addition of ethyl nitroacetate to isatin-derived N-Boc ketimines (Boc = tert-butoxycarbonyl), followed by the removal of the nitro group, is described. The scalable reaction sequence leads to the title compounds as important intermediates of pyrroloindoline alkaloids and related drugs in excellent yields and enantioselectivities. The synthesis of the hexahydrofurano[2,3-b]indole skeleton, the spirocarbamate oxindole unit, and the formal synthesis of AG-041R have been carried out to demonstrate the synthetic utility of this protocol.

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Authors+Show Affiliations

Zhao K
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany), Fax: (+49) 241-809-2127 http://www.oc.rwth-aachen.de/akenders/AKEN_D.HTM.
Shu T
No affiliation info available
Jia J
No affiliation info available
Raabe G
No affiliation info available
Enders D
No affiliation info available

MeSH

CatalysisFuransIminesIndole AlkaloidsIndolesMolecular StructureNitrilesOxindolesSpiro CompoundsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25630891

Citation

Zhao, Kun, et al. "An Organocatalytic Mannich/denitration Reaction for the Asymmetric Synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: Formal Synthesis of AG-041R." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 21, no. 10, 2015, pp. 3933-6.
Zhao K, Shu T, Jia J, et al. An organocatalytic Mannich/denitration reaction for the asymmetric synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: formal synthesis of AG-041R. Chemistry. 2015;21(10):3933-6.
Zhao, K., Shu, T., Jia, J., Raabe, G., & Enders, D. (2015). An organocatalytic Mannich/denitration reaction for the asymmetric synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: formal synthesis of AG-041R. Chemistry (Weinheim an Der Bergstrasse, Germany), 21(10), 3933-6. https://doi.org/10.1002/chem.201406422
Zhao K, et al. An Organocatalytic Mannich/denitration Reaction for the Asymmetric Synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: Formal Synthesis of AG-041R. Chemistry. 2015 Mar 2;21(10):3933-6. PubMed PMID: 25630891.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An organocatalytic Mannich/denitration reaction for the asymmetric synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: formal synthesis of AG-041R. AU - Zhao,Kun, AU - Shu,Tao, AU - Jia,Jiaqi, AU - Raabe,Gerhard, AU - Enders,Dieter, Y1 - 2015/01/28/ PY - 2014/10/10/received PY - 2015/1/30/entrez PY - 2015/1/30/pubmed PY - 2015/11/6/medline KW - Mannich reaction KW - asymmetric synthesis KW - ketimines KW - organocatalysis KW - oxindoles SP - 3933 EP - 6 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 21 IS - 10 N2 - The highly enantioselective organocatalytic addition of ethyl nitroacetate to isatin-derived N-Boc ketimines (Boc = tert-butoxycarbonyl), followed by the removal of the nitro group, is described. The scalable reaction sequence leads to the title compounds as important intermediates of pyrroloindoline alkaloids and related drugs in excellent yields and enantioselectivities. The synthesis of the hexahydrofurano[2,3-b]indole skeleton, the spirocarbamate oxindole unit, and the formal synthesis of AG-041R have been carried out to demonstrate the synthetic utility of this protocol. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25630891/An_organocatalytic_Mannich/denitration_reaction_for_the_asymmetric_synthesis_of_3_ethylacetate_substitued_3_amino_2_oxindoles:_formal_synthesis_of_AG_041R_ DB - PRIME DP - Unbound Medicine ER -