doi: 10.1021/ja9109105.
Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes
Affiliations
- PMID: 20158189
- DOI: 10.1021/ja9109105
Item in Clipboard
Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes
J Am Chem Soc.
.
Abstract
Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete gamma- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed.
Similar articles
-
Copper-catalyzed enantioselective allylic substitution with alkylboranes.J Am Chem Soc. 2012 Nov 14;134(45):18573-6. doi: 10.1021/ja3093955. Epub 2012 Oct 31. J Am Chem Soc. 2012. PMID: 23106350
-
Copper-catalyzed gamma-selective and stereospecific allyl-aryl coupling between (Z)-acyclic and cyclic allylic phosphates and arylboronates.Org Lett. 2010 May 21;12(10):2438-40. doi: 10.1021/ol100841y. Org Lett. 2010. PMID: 20429532
-
Highly site- and enantioselective Cu-catalyzed allylic alkylation reactions with easily accessible vinylaluminum reagents.J Am Chem Soc. 2008 Jan 16;130(2):446-7. doi: 10.1021/ja0782192. Epub 2007 Dec 19. J Am Chem Soc. 2008. PMID: 18088127 No abstract available.
-
Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents.Chem Rev. 2008 Aug;108(8):2824-52. doi: 10.1021/cr068424k. Chem Rev. 2008. PMID: 18698733 Review. No abstract available.
-
Copper-catalyzed divergent kinetic resolution of racemic allylic substrates.Chirality. 2011 Oct;23(9):703-10. doi: 10.1002/chir.20980. Epub 2011 Aug 12. Chirality. 2011. PMID: 21837639 Review.
Cited by
-
Asymmetric synthesis of γ-chiral borylalkanes via sequential reduction/hydroboration using a single copper catalyst.Chem Sci. 2020 Aug 6;11(33):8961-8965. doi: 10.1039/d0sc03759a. Chem Sci. 2020. PMID: 34123150 Free PMC article.
-
Catalytic SN2'- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis.Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3455-8. doi: 10.1002/anie.201600309. Epub 2016 Feb 4. Angew Chem Int Ed Engl. 2016. PMID: 26845488 Free PMC article.
-
Copper-Catalyzed Coupling of Alkyl Vicinal Bis(boronic Esters) to an Array of Electrophiles.J Am Chem Soc. 2022 Oct 5;144(39):17815-17823. doi: 10.1021/jacs.2c02817. Epub 2022 Sep 22. J Am Chem Soc. 2022. PMID: 36137527 Free PMC article.
-
Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates.Beilstein J Org Chem. 2015 Dec 4;11:2444-50. doi: 10.3762/bjoc.11.265. eCollection 2015. Beilstein J Org Chem. 2015. PMID: 26734092 Free PMC article.
-
Recent advances in allylation of chiral secondary alkylcopper species.Beilstein J Org Chem. 2025 Mar 20;21:639-658. doi: 10.3762/bjoc.21.51. eCollection 2025. Beilstein J Org Chem. 2025. PMID: 40130179 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
