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Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones.
Org Lett. 2009 Jan 01; 11(1):117-20.OL

Abstract

An efficient and highly regioselective route to synthesize polysubstituted 1,3,4-alkatrien-2-yl cyclopropane derivatives via Pd(0)-catalyzed highly regioselective coupling cyclization of (2,3-butadienyl)malonate or bis(phenylsulfonyl)methane with propargylic carbonates was reported. The reaction proceeded smoothly under neutral conditions to afford the products in 73-96% yields. The products may be efficiently converted to cyclopentenone derivatives via a catalytic Pauson-Khand reaction under ambient conditions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shu W
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China.
Jia G
No affiliation info available
Ma S
No affiliation info available

MeSH

AlkynesCarbonatesCatalysisCyclizationCyclopentanesCyclopropanesMalonatesMolecular StructureOrganometallic CompoundsPalladiumPropanolsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19053848

Citation

Shu, Wei, et al. "Palladium-catalyzed Regioselective Cyclopropanating Allenylation of (2,3-butadienyl)malonates With Propargylic Carbonates and Their Application to Synthesize Cyclopentenones." Organic Letters, vol. 11, no. 1, 2009, pp. 117-20.
Shu W, Jia G, Ma S. Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones. Org Lett. 2009;11(1):117-20.
Shu, W., Jia, G., & Ma, S. (2009). Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones. Organic Letters, 11(1), 117-20. https://doi.org/10.1021/ol802465k
Shu W, Jia G, Ma S. Palladium-catalyzed Regioselective Cyclopropanating Allenylation of (2,3-butadienyl)malonates With Propargylic Carbonates and Their Application to Synthesize Cyclopentenones. Org Lett. 2009 Jan 1;11(1):117-20. PubMed PMID: 19053848.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed regioselective cyclopropanating allenylation of (2,3-butadienyl)malonates with propargylic carbonates and their application to synthesize cyclopentenones. AU - Shu,Wei, AU - Jia,Guochen, AU - Ma,Shengming, PY - 2008/12/5/pubmed PY - 2009/2/12/medline PY - 2008/12/5/entrez SP - 117 EP - 20 JF - Organic letters JO - Org Lett VL - 11 IS - 1 N2 - An efficient and highly regioselective route to synthesize polysubstituted 1,3,4-alkatrien-2-yl cyclopropane derivatives via Pd(0)-catalyzed highly regioselective coupling cyclization of (2,3-butadienyl)malonate or bis(phenylsulfonyl)methane with propargylic carbonates was reported. The reaction proceeded smoothly under neutral conditions to afford the products in 73-96% yields. The products may be efficiently converted to cyclopentenone derivatives via a catalytic Pauson-Khand reaction under ambient conditions. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19053848/Palladium_catalyzed_regioselective_cyclopropanating_allenylation_of__23_butadienyl_malonates_with_propargylic_carbonates_and_their_application_to_synthesize_cyclopentenones_ DB - PRIME DP - Unbound Medicine ER -