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Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles.
J Org Chem. 2021 08 06; 86(15):10799-10811.JO

Abstract

An enantioselective palladium-catalyzed annulation of alkyne-tethered malononitriles for the synthesis of 3,4-ring-fused isocoumarins is described. This cascade strategy involves oxypalladation of ortho-alkynylbenzoates and desymmetrizing addition onto one cyano group of the pendant malononitriles, which enables the concurrent construction of two rings and an all-carbon quaternary stereocenter in a single operation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang H
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.
Li W
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.
Hu XD
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.
Liu WB
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), and College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China.

MeSH

AlkynesCatalysisIsocoumarinsMolecular StructureNitrilesPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

34255511

Citation

Zhang, Hui, et al. "Enantioselective Synthesis of Fused Isocoumarins Via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles." The Journal of Organic Chemistry, vol. 86, no. 15, 2021, pp. 10799-10811.
Zhang H, Li W, Hu XD, et al. Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles. J Org Chem. 2021;86(15):10799-10811.
Zhang, H., Li, W., Hu, X. D., & Liu, W. B. (2021). Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles. The Journal of Organic Chemistry, 86(15), 10799-10811. https://doi.org/10.1021/acs.joc.1c01026
Zhang H, et al. Enantioselective Synthesis of Fused Isocoumarins Via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles. J Org Chem. 2021 08 6;86(15):10799-10811. PubMed PMID: 34255511.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles. AU - Zhang,Hui, AU - Li,Weishuang, AU - Hu,Xu-Dong, AU - Liu,Wen-Bo, Y1 - 2021/07/13/ PY - 2021/7/14/pubmed PY - 2021/10/6/medline PY - 2021/7/13/entrez SP - 10799 EP - 10811 JF - The Journal of organic chemistry JO - J Org Chem VL - 86 IS - 15 N2 - An enantioselective palladium-catalyzed annulation of alkyne-tethered malononitriles for the synthesis of 3,4-ring-fused isocoumarins is described. This cascade strategy involves oxypalladation of ortho-alkynylbenzoates and desymmetrizing addition onto one cyano group of the pendant malononitriles, which enables the concurrent construction of two rings and an all-carbon quaternary stereocenter in a single operation. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/34255511/Enantioselective_Synthesis_of_Fused_Isocoumarins_via_Palladium_Catalyzed_Annulation_of_Alkyne_Tethered_Malononitriles_ DB - PRIME DP - Unbound Medicine ER -