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Palladium-catalyzed asymmetric cycloadditions of vinylcyclopropanes and in situ formed unsaturated imines: construction of structurally and optically enriched spiroindolenines.
Org Lett. 2015 Jan 02; 17(1):150-3.OL

Abstract

A palladium-catalyzed (3 + 2) cycloaddition of vinyl cyclopropane and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles is reported. The reaction proceeds with high diastereoselectivity to provide the optically enriched spirocyclopentane-1,3'-indolenines in up to 74% yield and with up to 97% ee, which contains an all-carbon quaternary center and two tertiary stereocenters. The reaction involves a first conjugate addition of the carbon anion of zwitterionic π-allylpalladium complex from vinyl cyclopropane to the in situ formed unsaturated imine followed by a palladium-catalyzed intramolecular C3-allylation of indole.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu ZS
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University , Nanchong 637002, P. R. China.
Li WK
No affiliation info available
Kang TR
No affiliation info available
He L
No affiliation info available
Liu QZ
No affiliation info available

MeSH

CatalysisCycloaddition ReactionCyclopropanesIminesIndolesMolecular StructurePalladiumSpiro CompoundsStereoisomerismSulfonesVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

25525709

Citation

Liu, Ze-Shui, et al. "Palladium-catalyzed Asymmetric Cycloadditions of Vinylcyclopropanes and in Situ Formed Unsaturated Imines: Construction of Structurally and Optically Enriched Spiroindolenines." Organic Letters, vol. 17, no. 1, 2015, pp. 150-3.
Liu ZS, Li WK, Kang TR, et al. Palladium-catalyzed asymmetric cycloadditions of vinylcyclopropanes and in situ formed unsaturated imines: construction of structurally and optically enriched spiroindolenines. Org Lett. 2015;17(1):150-3.
Liu, Z. S., Li, W. K., Kang, T. R., He, L., & Liu, Q. Z. (2015). Palladium-catalyzed asymmetric cycloadditions of vinylcyclopropanes and in situ formed unsaturated imines: construction of structurally and optically enriched spiroindolenines. Organic Letters, 17(1), 150-3. https://doi.org/10.1021/ol503383x
Liu ZS, et al. Palladium-catalyzed Asymmetric Cycloadditions of Vinylcyclopropanes and in Situ Formed Unsaturated Imines: Construction of Structurally and Optically Enriched Spiroindolenines. Org Lett. 2015 Jan 2;17(1):150-3. PubMed PMID: 25525709.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed asymmetric cycloadditions of vinylcyclopropanes and in situ formed unsaturated imines: construction of structurally and optically enriched spiroindolenines. AU - Liu,Ze-Shui, AU - Li,Wen-Ke, AU - Kang,Tai-Ran, AU - He,Long, AU - Liu,Quan-Zhong, Y1 - 2014/12/19/ PY - 2014/12/20/entrez PY - 2014/12/20/pubmed PY - 2015/3/7/medline SP - 150 EP - 3 JF - Organic letters JO - Org Lett VL - 17 IS - 1 N2 - A palladium-catalyzed (3 + 2) cycloaddition of vinyl cyclopropane and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles is reported. The reaction proceeds with high diastereoselectivity to provide the optically enriched spirocyclopentane-1,3'-indolenines in up to 74% yield and with up to 97% ee, which contains an all-carbon quaternary center and two tertiary stereocenters. The reaction involves a first conjugate addition of the carbon anion of zwitterionic π-allylpalladium complex from vinyl cyclopropane to the in situ formed unsaturated imine followed by a palladium-catalyzed intramolecular C3-allylation of indole. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25525709/Palladium_catalyzed_asymmetric_cycloadditions_of_vinylcyclopropanes_and_in_situ_formed_unsaturated_imines:_construction_of_structurally_and_optically_enriched_spiroindolenines_ DB - PRIME DP - Unbound Medicine ER -