title: Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.
abstract: A new catalytic synthesis of densely-substituted tetrahydroquinolines is described. This reaction forms up to two rings, three bonds, and three stereogenic centers with excellent stereo- and regiocontrol in a single step. Although control experiments demonstrate that the active catalyst is protic acid, Sc(OTf)3serves as an effective and practical pre-catalyst. The scope of this reaction is demonstrated with 21 monocyclizations and 14 bicyclization reactions.
authors.affiliation: Department of Chemistry, University of California, 1 Shields Ave, Davis, CA, 95618 USA.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Moore
authors.forename: Cristian
authors.initials: C
authors.lastname: Soldi
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
references.citation: J Am Chem Soc. 2010 Jun 23;132(24):8276-7
references.pmid: 20518531
references.citation: Chem Commun (Camb). 2005 Jul 7;(25):3162-4
references.pmid: 15968358
references.citation: Chem Rev. 2007 Dec;107(12):5744-58
references.pmid: 17983247
references.citation: J Org Chem. 2005 Feb 4;70(3):925-31
references.pmid: 15675850
references.citation: J Am Chem Soc. 1976 Feb 18;98(4):1039-4
references.pmid: 1245704
references.citation: Angew Chem Int Ed Engl. 2012 Oct 15;51(42):10619-23
references.pmid: 22987395
references.citation: Angew Chem Int Ed Engl. 2009;48(24):4363-6
references.pmid: 19437518
references.citation: J Am Chem Soc. 2011 Oct 5;133(39):15308-11
references.pmid: 21859086
references.citation: J Am Chem Soc. 2006 Aug 2;128(30):9626-7
references.pmid: 16866505
references.citation: J Am Chem Soc. 2010 Nov 10;132(44):15752-65
references.pmid: 20961070
references.citation: Nature. 2007 Feb 22;445(7130):900-3
references.pmid: 17314976
references.citation: J Am Chem Soc. 2004 Mar 24;126(11):3416-7
references.pmid: 15025456
references.citation: Org Lett. 2012 Jun 1;14(11):2750-3
references.pmid: 22578075
references.citation: Org Lett. 2010 Aug 6;12(15):3548-51
references.pmid: 20670018
references.citation: J Am Chem Soc. 2007 Jan 24;129(3):492-3
references.pmid: 17227003
references.citation: Angew Chem Int Ed Engl. 2009;48(7):1244-7
references.pmid: 19137523
references.citation: Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6706-20
references.pmid: 21678531
references.citation: Angew Chem Int Ed Engl. 2008;47(32):6011-4
references.pmid: 18649296
references.citation: Chem Rev. 2005 Dec;105(12):4730-56
references.pmid: 16351060
references.citation: Org Lett. 2006 Nov 23;8(24):5649-52
references.pmid: 17107094
references.citation: Org Lett. 2005 Feb 3;7(3):451-3
references.pmid: 15673262
references.citation: J Am Chem Soc. 2007 Oct 3;129(39):11880-1
references.pmid: 17850150