Lewis acid mediated intramolecular C-C bond formation of alkyne-epoxide leading to six-membered nitrogen and oxygen heterocycles
- PMID: 24720735
- DOI: 10.1021/jo402550e
Lewis acid mediated intramolecular C-C bond formation of alkyne-epoxide leading to six-membered nitrogen and oxygen heterocycles
Abstract
Intramolecular C-C bond formation of oxygen- and nitrogen-tethered alkynes and epoxide mediated by Lewis acid under ambient conditions is described. A simple procedure for the synthesis of 3,6- and 5,6-dihydropyrans and 3,4-dehydropiperidines from acyclic building blocks in good yields without using any transition metal is shown.
Similar articles
-
Highly regioselective Lewis acid-catalyzed [3+2] cycloaddition of alkynes with donor-acceptor oxiranes by selective carbon-carbon bond cleavage of epoxides.Chem Commun (Camb). 2011 Dec 28;47(48):12870-2. doi: 10.1039/c1cc15669a. Epub 2011 Nov 9. Chem Commun (Camb). 2011. PMID: 22068307
-
Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.J Org Chem. 2011 Nov 18;76(22):9269-77. doi: 10.1021/jo201478d. Epub 2011 Oct 25. J Org Chem. 2011. PMID: 21916500 Free PMC article.
-
Diastereoselective synthesis of CF3-substituted, epoxide-fused heterocycles with β-(trifluoromethyl)vinylsulfonium salts.Org Lett. 2012 Dec 21;14(24):6370-3. doi: 10.1021/ol303200n. Epub 2012 Dec 11. Org Lett. 2012. PMID: 23231752
-
Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.Org Biomol Chem. 2022 Feb 9;20(6):1150-1175. doi: 10.1039/d1ob01905h. Org Biomol Chem. 2022. PMID: 35029626 Free PMC article. Review.
-
Hydroarylation of alkynes catalyzed by nickel.Chem Rec. 2011 Sep;11(5):242-51. doi: 10.1002/tcr.201100023. Epub 2011 Sep 6. Chem Rec. 2011. PMID: 21898779 Review.
Cited by
-
Stereo- and Regioselective Synthesis of 4-Vinylpyrrolidine from N-Tethered Alkyne-Alkenol.ACS Omega. 2018 Jan 18;3(1):576-584. doi: 10.1021/acsomega.7b01785. eCollection 2018 Jan 31. ACS Omega. 2018. PMID: 31457915 Free PMC article.
-
Vinylsilanes in Highly Diastereo- and Regio-Selective Synthesis of Dihydropyrans.ACS Omega. 2019 Feb 4;4(2):2630-2636. doi: 10.1021/acsomega.8b03635. eCollection 2019 Feb 28. ACS Omega. 2019. PMID: 31459498 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources