title: Gold (III) Chloride-Catalyzed 6-endo-trigOxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.
abstract: Alkynones were treated with boron trifluoride diethyl etherate to generate β-iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa-Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyran-containing ring systems.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, NY 14627, USA.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Ciesielski
authors.forename: David
authors.initials: D
authors.lastname: Lebœuf
authors.forename: Harry A
authors.initials: HA
authors.lastname: Stern
authors.forename: Alison J
authors.initials: AJ
authors.lastname: Frontier
keywords: cyclization; gold; oxa-Michael; tetrahydropyranone
references.citation: Angew Chem Int Ed Engl. 2007;46(19):3410-49
references.pmid: 17427893
references.citation: J Am Chem Soc. 2004 May 19;126(19):5964-5
references.pmid: 15137751
references.citation: Chem Rev. 2011 Mar 9;111(3):1954-93
references.pmid: 21391568
references.citation: Chem Rev. 2008 Aug;108(8):3266-325
references.pmid: 18651778
references.citation: Org Lett. 2004 Apr 15;6(8):1289-92
references.pmid: 15070319
references.citation: Chem Soc Rev. 2012 Feb 7;41(3):988-99
references.pmid: 21796323
references.citation: Chem Rev. 2008 Aug;108(8):3239-65
references.pmid: 18613729
references.citation: J Org Chem. 2011 Aug 19;76(16):6534-41
references.pmid: 21739982
references.citation: Org Lett. 2001 May 17;3(10):1491-4
references.pmid: 11388849
references.citation: Chem Rev. 2008 Aug;108(8):3351-78
references.pmid: 18652511
references.citation: Chem Soc Rev. 2008 Jun;37(6):1218-28
references.pmid: 18497934
references.citation: Chemistry. 2006 Sep 18;12(27):7190-203
references.pmid: 16819725
references.citation: Org Lett. 2012 Aug 17;14(16):4082-5
references.pmid: 22853449
references.citation: Org Lett. 2009 Oct 1;11(19):4374-7
references.pmid: 19736911
references.citation: Org Lett. 2009 Apr 2;11(7):1591-4
references.pmid: 19260663
references.citation: Org Lett. 2011 Jan 21;13(2):248-51
references.pmid: 21162546
references.citation: Chem Soc Rev. 2009 Nov;38(11):3208-21
references.pmid: 19847352
references.citation: Chem Commun (Camb). 2013 Jan 7;49(2):193-5
references.pmid: 23168684
references.citation: Chem Rev. 2011 Mar 9;111(3):1657-712
references.pmid: 21391565
references.citation: J Am Chem Soc. 2003 Feb 19;125(7):1712-3
references.pmid: 12580592
references.citation: Tetrahedron Lett. 2007 Jun 25;48(26):4605-4607
references.pmid: 18575571
references.citation: Chem Rev. 2008 Aug;108(8):3326-50
references.pmid: 18636778
references.citation: J Org Chem. 2007 Oct 12;72(21):7817-31
references.pmid: 17579452
references.citation: Chem Commun (Camb). 2002 Aug 21;(16):1736-7
references.pmid: 12196974
references.citation: Angew Chem Int Ed Engl. 2001 Nov 5;40(21):4055-4060
references.pmid: 12404491
references.citation: Angew Chem Int Ed Engl. 2006 Dec 4;45(47):7896-936
references.pmid: 17131371
references.citation: Org Lett. 2000 Aug 10;2(16):2507-9
references.pmid: 10956533
references.citation: Org Lett. 2001 Sep 20;3(19):2949-51
references.pmid: 11554815
references.citation: J Am Chem Soc. 2005 Aug 3;127(30):10500-1
references.pmid: 16045332
references.citation: Chem Rev. 2011 Mar 9;111(3):1994-2009
references.pmid: 21314182
references.citation: J Org Chem. 2011 Sep 2;76(17):7027-39
references.pmid: 21819039
references.citation: Angew Chem Int Ed Engl. 2008;47(23):4268-315
references.pmid: 18381724
references.citation: Tetrahedron. 2011 Dec 30;67(52):10105-10118
references.pmid: 23750054
references.citation: Chem Rev. 2007 Jul;107(7):3180-211
references.pmid: 17580975