Gold(I)-catalyzed stereoselective olefin cyclopropanation
- PMID: 16366541
- DOI: 10.1021/ja0552500
Gold(I)-catalyzed stereoselective olefin cyclopropanation
Abstract
A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)-carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinyl cyclopropanes with high cis-selectivity.
Similar articles
-
Gold(I)-catalyzed intermolecular cyclopropanation of enynes with alkenes: trapping of two different gold carbenes.Angew Chem Int Ed Engl. 2006 Sep 11;45(36):6029-32. doi: 10.1002/anie.200602448. Angew Chem Int Ed Engl. 2006. PMID: 16900550 No abstract available.
-
Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.J Am Chem Soc. 2005 Dec 28;127(51):18014-5. doi: 10.1021/ja056192l. J Am Chem Soc. 2005. PMID: 16366547
-
Rhodium N-confused porphyrin-catalyzed alkene cyclopropanation.Chem Commun (Camb). 2006 Nov 4;(41):4335-7. doi: 10.1039/b608154a. Epub 2006 Sep 5. Chem Commun (Camb). 2006. PMID: 17047859
-
Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.Chem Rev. 2008 Aug;108(8):3326-50. doi: 10.1021/cr0684319. Epub 2008 Jul 18. Chem Rev. 2008. PMID: 18636778 Review. No abstract available.
-
Gold-catalyzed organic transformations.Chem Rev. 2008 Aug;108(8):3239-65. doi: 10.1021/cr068434l. Epub 2008 Jul 10. Chem Rev. 2008. PMID: 18613729 Review. No abstract available.
Cited by
-
Control of selectivity in heterogeneous catalysis by tuning nanoparticle properties and reactor residence time.Nat Chem. 2012 Nov;4(11):947-52. doi: 10.1038/nchem.1465. Epub 2012 Sep 30. Nat Chem. 2012. PMID: 23089871
-
Anatomy of gold catalysts: facts and myths.Org Biomol Chem. 2015 Jul 14;13(26):7103-18. doi: 10.1039/c5ob00736d. Epub 2015 Jun 9. Org Biomol Chem. 2015. PMID: 26055272 Free PMC article.
-
Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".Chem Soc Rev. 2012 Dec 7;41(23):7698-711. doi: 10.1039/c2cs35235d. Chem Soc Rev. 2012. PMID: 22895533 Free PMC article. Review.
-
Intriguing mechanistic labyrinths in gold(I) catalysis.Chem Commun (Camb). 2014 Jan 4;50(1):16-28. doi: 10.1039/c3cc45518a. Chem Commun (Camb). 2014. PMID: 24176910 Free PMC article.
-
Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes.Beilstein J Org Chem. 2013 Sep 24;9:1925-30. doi: 10.3762/bjoc.9.227. eCollection 2013. Beilstein J Org Chem. 2013. PMID: 24204402 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources