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Palladium(II)-catalyzed intramolecular 1,4-oxyacyloxylation of conjugated dienes. A stereocontrolled route to fused six-membered lactones and pyrans.
J Org Chem. 2004 Apr 30; 69(9):3102-11.JO

Abstract

Stereocontrolled palladium(II)-catalyzed intramolecular 1,4-oxidations of dienyl acids and alcohols proceed under mild conditions to give fused delta-lactones and pyrans, respectively, in good yields. The stereo- and regioselectivity was affected by the presence of LiCl and solvent composition (HOAc/acetone). The products obtained were used for further functionalizations using copper(I)-mediated reactions. Stoichiometric reactions of preformed dibutylcyanocuprates with pyrans containing an allylic acetate gave cis- and trans-fused ring systems with high gamma-selectivity and in high yields.

Authors+Show Affiliations

Verboom RC
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
Persson BA
No affiliation info available
Bäckvall JE
No affiliation info available

MeSH

AcylationAlkadienesCarboxylic AcidsCatalysisCopperCyclizationLactonesLithium ChlorideMolecular StructureOrganometallic CompoundsOxidation-ReductionPalladiumPyransSolventsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15104449

Citation

Verboom, Renzo C., et al. "Palladium(II)-catalyzed Intramolecular 1,4-oxyacyloxylation of Conjugated Dienes. a Stereocontrolled Route to Fused Six-membered Lactones and Pyrans." The Journal of Organic Chemistry, vol. 69, no. 9, 2004, pp. 3102-11.
Verboom RC, Persson BA, Bäckvall JE. Palladium(II)-catalyzed intramolecular 1,4-oxyacyloxylation of conjugated dienes. A stereocontrolled route to fused six-membered lactones and pyrans. J Org Chem. 2004;69(9):3102-11.
Verboom, R. C., Persson, B. A., & Bäckvall, J. E. (2004). Palladium(II)-catalyzed intramolecular 1,4-oxyacyloxylation of conjugated dienes. A stereocontrolled route to fused six-membered lactones and pyrans. The Journal of Organic Chemistry, 69(9), 3102-11.
Verboom RC, Persson BA, Bäckvall JE. Palladium(II)-catalyzed Intramolecular 1,4-oxyacyloxylation of Conjugated Dienes. a Stereocontrolled Route to Fused Six-membered Lactones and Pyrans. J Org Chem. 2004 Apr 30;69(9):3102-11. PubMed PMID: 15104449.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(II)-catalyzed intramolecular 1,4-oxyacyloxylation of conjugated dienes. A stereocontrolled route to fused six-membered lactones and pyrans. AU - Verboom,Renzo C, AU - Persson,B Anders, AU - Bäckvall,Jan-E, PY - 2004/4/24/pubmed PY - 2004/7/14/medline PY - 2004/4/24/entrez SP - 3102 EP - 11 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 9 N2 - Stereocontrolled palladium(II)-catalyzed intramolecular 1,4-oxidations of dienyl acids and alcohols proceed under mild conditions to give fused delta-lactones and pyrans, respectively, in good yields. The stereo- and regioselectivity was affected by the presence of LiCl and solvent composition (HOAc/acetone). The products obtained were used for further functionalizations using copper(I)-mediated reactions. Stoichiometric reactions of preformed dibutylcyanocuprates with pyrans containing an allylic acetate gave cis- and trans-fused ring systems with high gamma-selectivity and in high yields. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15104449/Palladium_II__catalyzed_intramolecular_14_oxyacyloxylation_of_conjugated_dienes__A_stereocontrolled_route_to_fused_six_membered_lactones_and_pyrans_ DB - PRIME DP - Unbound Medicine ER -