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N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles.
Org Lett. 2014 Jun 20; 16(12):3272-5.OL

Abstract

A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Xu J
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
Mou C
No affiliation info available
Zhu T
No affiliation info available
Song BA
No affiliation info available
Chi YR
No affiliation info available

MeSH

Aza CompoundsBenzoinCatalysisIminesIndolesIsatinMethaneMolecular StructureNitrilesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24877668

Citation

Xu, Jianfeng, et al. "N-Heterocyclic Carbene-catalyzed Chemoselective Cross-aza-benzoin Reaction of Enals With Isatin-derived Ketimines: Access to Chiral Quaternary Aminooxindoles." Organic Letters, vol. 16, no. 12, 2014, pp. 3272-5.
Xu J, Mou C, Zhu T, et al. N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles. Org Lett. 2014;16(12):3272-5.
Xu, J., Mou, C., Zhu, T., Song, B. A., & Chi, Y. R. (2014). N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles. Organic Letters, 16(12), 3272-5. https://doi.org/10.1021/ol501286e
Xu J, et al. N-Heterocyclic Carbene-catalyzed Chemoselective Cross-aza-benzoin Reaction of Enals With Isatin-derived Ketimines: Access to Chiral Quaternary Aminooxindoles. Org Lett. 2014 Jun 20;16(12):3272-5. PubMed PMID: 24877668.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles. AU - Xu,Jianfeng, AU - Mou,Chengli, AU - Zhu,Tingshun, AU - Song,Bao-An, AU - Chi,Yonggui Robin, Y1 - 2014/05/30/ PY - 2014/6/1/entrez PY - 2014/6/1/pubmed PY - 2014/8/16/medline SP - 3272 EP - 5 JF - Organic letters JO - Org Lett VL - 16 IS - 12 N2 - A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24877668/N_Heterocyclic_carbene_catalyzed_chemoselective_cross_aza_benzoin_reaction_of_enals_with_isatin_derived_ketimines:_access_to_chiral_quaternary_aminooxindoles_ DB - PRIME DP - Unbound Medicine ER -