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Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.
Org Lett. 2020 10 02; 22(19):7409-7414.OL

Abstract

The copper-catalyzed enantioselective intramolecular hydroalkoxylation of unactivated alkenes for the synthesis of tetrahydrofurans, phthalans, isochromans, and morpholines from 4- and 5-alkenols is reported. The substrate scope is complementary to existing enantioselective alkene hydroalkoxylations and is broad with respect to substrate backbone and alkene substitution. The asymmetric induction and isotopic labeling studies support a polar/radical mechanism involving enantioselective oxycupration followed by C-[Cu] homolysis and hydrogen atom transfer. Synthesis of the antifungal insecticide furametpyr was accomplished.

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Authors+Show Affiliations

Chen D
Chemistry Department, State University of New York at Buffalo, Buffalo, New York 14260, United States.
Berhane IA
Chemistry Department, State University of New York at Buffalo, Buffalo, New York 14260, United States.
Chemler SR
Chemistry Department, State University of New York at Buffalo, Buffalo, New York 14260, United States.

MeSH

AlkenesAntifungal AgentsBenzofuransCatalysisCopperEthers, CyclicFuransHydrogenInsecticidesMolecular StructurePyrazolesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32496794

Citation

Chen, Dake, et al. "Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers." Organic Letters, vol. 22, no. 19, 2020, pp. 7409-7414.
Chen D, Berhane IA, Chemler SR. Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers. Org Lett. 2020;22(19):7409-7414.
Chen, D., Berhane, I. A., & Chemler, S. R. (2020). Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers. Organic Letters, 22(19), 7409-7414. https://doi.org/10.1021/acs.orglett.0c01691
Chen D, Berhane IA, Chemler SR. Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers. Org Lett. 2020 10 2;22(19):7409-7414. PubMed PMID: 32496794.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers. AU - Chen,Dake, AU - Berhane,Ilyas A, AU - Chemler,Sherry R, Y1 - 2020/06/04/ PY - 2020/6/5/pubmed PY - 2021/8/5/medline PY - 2020/6/5/entrez SP - 7409 EP - 7414 JF - Organic letters JO - Org Lett VL - 22 IS - 19 N2 - The copper-catalyzed enantioselective intramolecular hydroalkoxylation of unactivated alkenes for the synthesis of tetrahydrofurans, phthalans, isochromans, and morpholines from 4- and 5-alkenols is reported. The substrate scope is complementary to existing enantioselective alkene hydroalkoxylations and is broad with respect to substrate backbone and alkene substitution. The asymmetric induction and isotopic labeling studies support a polar/radical mechanism involving enantioselective oxycupration followed by C-[Cu] homolysis and hydrogen atom transfer. Synthesis of the antifungal insecticide furametpyr was accomplished. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/32496794/Copper_Catalyzed_Enantioselective_Hydroalkoxylation_of_Alkenols_for_the_Synthesis_of_Cyclic_Ethers_ DB - PRIME DP - Unbound Medicine ER -