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Dual amine and palladium catalysis in diastereo- and enantioselective allene carbocyclization reactions.
Org Lett. 2012 Dec 21; 14(24):6350-3.OL

Abstract

A pyrrolidine and Pd catalyzed diastereoselective carbocyclization of aldehyde and ketone-linked allenes has been developed. The cooperative organo/metal-catalyzed cyclization reaction, which presumably proceeds via an enamine intermediate, is efficient and broad in scope. Also, it has been extended to a catalytic asymmetric variant using diarylprolinol-based organocatalysts to afford substituted cyclopentane and pyrrolidine reaction products in up to 82% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li M
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
Datta S
No affiliation info available
Barber DM
No affiliation info available
Dixon DJ
No affiliation info available

MeSH

AldehydesAminesCatalysisCyclizationCyclopentanesKetonesMagnetic Resonance SpectroscopyMolecular StructurePalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23214932

Citation

Li, Meiling, et al. "Dual Amine and Palladium Catalysis in Diastereo- and Enantioselective Allene Carbocyclization Reactions." Organic Letters, vol. 14, no. 24, 2012, pp. 6350-3.
Li M, Datta S, Barber DM, et al. Dual amine and palladium catalysis in diastereo- and enantioselective allene carbocyclization reactions. Org Lett. 2012;14(24):6350-3.
Li, M., Datta, S., Barber, D. M., & Dixon, D. J. (2012). Dual amine and palladium catalysis in diastereo- and enantioselective allene carbocyclization reactions. Organic Letters, 14(24), 6350-3. https://doi.org/10.1021/ol303128s
Li M, et al. Dual Amine and Palladium Catalysis in Diastereo- and Enantioselective Allene Carbocyclization Reactions. Org Lett. 2012 Dec 21;14(24):6350-3. PubMed PMID: 23214932.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Dual amine and palladium catalysis in diastereo- and enantioselective allene carbocyclization reactions. AU - Li,Meiling, AU - Datta,Swarup, AU - Barber,David M, AU - Dixon,Darren J, Y1 - 2012/12/06/ PY - 2012/12/11/entrez PY - 2012/12/12/pubmed PY - 2013/3/21/medline SP - 6350 EP - 3 JF - Organic letters JO - Org Lett VL - 14 IS - 24 N2 - A pyrrolidine and Pd catalyzed diastereoselective carbocyclization of aldehyde and ketone-linked allenes has been developed. The cooperative organo/metal-catalyzed cyclization reaction, which presumably proceeds via an enamine intermediate, is efficient and broad in scope. Also, it has been extended to a catalytic asymmetric variant using diarylprolinol-based organocatalysts to afford substituted cyclopentane and pyrrolidine reaction products in up to 82% ee. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23214932/Dual_amine_and_palladium_catalysis_in_diastereo__and_enantioselective_allene_carbocyclization_reactions_ DB - PRIME DP - Unbound Medicine ER -