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Diastereoselective syntheses of functionalized five-membered carbocycles and heterocycles by a SmI2-promoted intramolecular coupling of bromoalkynes and alpha,beta-unsaturated esters.
Org Lett. 2010 Jul 02; 12(13):3026-9.OL

Abstract

An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Takahashi K
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.
Honda T
No affiliation info available

MeSH

AlkynesEstersHeterocyclic CompoundsHydrocarbons, BrominatedHydrocarbons, CyclicMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20515018

Citation

Takahashi, Kazunori, and Toshio Honda. "Diastereoselective Syntheses of Functionalized Five-membered Carbocycles and Heterocycles By a SmI2-promoted Intramolecular Coupling of Bromoalkynes and Alpha,beta-unsaturated Esters." Organic Letters, vol. 12, no. 13, 2010, pp. 3026-9.
Takahashi K, Honda T. Diastereoselective syntheses of functionalized five-membered carbocycles and heterocycles by a SmI2-promoted intramolecular coupling of bromoalkynes and alpha,beta-unsaturated esters. Org Lett. 2010;12(13):3026-9.
Takahashi, K., & Honda, T. (2010). Diastereoselective syntheses of functionalized five-membered carbocycles and heterocycles by a SmI2-promoted intramolecular coupling of bromoalkynes and alpha,beta-unsaturated esters. Organic Letters, 12(13), 3026-9. https://doi.org/10.1021/ol101034s
Takahashi K, Honda T. Diastereoselective Syntheses of Functionalized Five-membered Carbocycles and Heterocycles By a SmI2-promoted Intramolecular Coupling of Bromoalkynes and Alpha,beta-unsaturated Esters. Org Lett. 2010 Jul 2;12(13):3026-9. PubMed PMID: 20515018.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Diastereoselective syntheses of functionalized five-membered carbocycles and heterocycles by a SmI2-promoted intramolecular coupling of bromoalkynes and alpha,beta-unsaturated esters. AU - Takahashi,Kazunori, AU - Honda,Toshio, PY - 2010/6/3/entrez PY - 2010/6/3/pubmed PY - 2010/9/21/medline SP - 3026 EP - 9 JF - Organic letters JO - Org Lett VL - 12 IS - 13 N2 - An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20515018/Diastereoselective_syntheses_of_functionalized_five_membered_carbocycles_and_heterocycles_by_a_SmI2_promoted_intramolecular_coupling_of_bromoalkynes_and_alphabeta_unsaturated_esters_ DB - PRIME DP - Unbound Medicine ER -