title: Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.
abstract: A Brønsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a β-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.
authors: Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
authors: Jingqi
authors: J
authors: Wang
authors: Erika A
authors: EA
authors: Crane
authors: Karl A
authors: KA
authors: Scheidt
references: Org Lett. 2009 Aug 20;11(16):3754-6
references: 19637858
references: J Am Chem Soc. 2008 Jan 23;130(3):804-5
references: 18161979
references: Chem Commun (Camb). 2010 Oct 7;46(37):6953-5
references: 20730196
references: Chem Commun (Camb). 2005 May 28;(20):2621-3
references: 15900347
references: Org Lett. 2010 Feb 5;12(3):572-5
references: 20050598
references: Angew Chem Int Ed Engl. 2010 Nov 2;49(45):8316-26
references: 20931580
references: Angew Chem Int Ed Engl. 1999 Nov 2;38(21):3186-3189
references: 10556897
references: J Comb Chem. 2010 Sep 13;12(5):659-63
references: 20593846
references: J Am Chem Soc. 2010 Jun 2;132(21):7508-13
references: 20450179
references: J Am Chem Soc. 2009 Sep 2;131(34):12406-14
references: 19663512
references: Angew Chem Int Ed Engl. 2010;49(4):744-7
references: 20029857
references: J Am Chem Soc. 2004 Nov 3;126(43):14095-104
references: 15506774
references: J Org Chem. 2010 Oct 1;75(19):6720-3
references: 20825233
references: J Am Chem Soc. 2006 Aug 16;128(32):10572-88
references: 16895426
references: J Am Chem Soc. 2009 May 27;131(20):6946-8
references: 19453193
references: ACS Med Chem Lett. 2010 Nov 11;1(8):400-405
references: 21116437
references: J Org Chem. 2006 Mar 17;71(6):2346-51
references: 16526783
references: Org Lett. 2004 Dec 23;6(26):4893-5
references: 15606093
references: Angew Chem Int Ed Engl. 2005 Mar 18;44(13):1924-42
references: 15770618
references: J Org Chem. 2009 Jan 2;74(1):283-8
references: 19053604
references: Org Lett. 2005 Mar 17;7(6):1113-6
references: 15760152
references: J Am Chem Soc. 2009 Sep 30;131(38):13819-25
references: 19736987
references: J Org Chem. 2010 Oct 1;75(19):6693-5
references: 20804180
references: Org Lett. 2009 Aug 6;11(15):3362-5
references: 19719184
references: J Org Chem. 2006 Mar 31;71(7):2587-99
references: 16555809
references: J Org Chem. 2001 Jun 29;66(13):4679-86
references: 11421792
references: Angew Chem Int Ed Engl. 2007;46(46):8748-58
references: 17943924
references: Org Lett. 2006 Jun 22;8(13):2715-8
references: 16774239
references: Org Lett. 2009 Nov 5;11(21):4910-3
references: 19799447
references: Org Lett. 2002 Mar 21;4(6):953-5
references: 11893194
references: Chem Commun (Camb). 2007 Feb 14;(6):631-3
references: 17264914
references: Org Lett. 2009 Aug 6;11(15):3366-9
references: 19719185
references: J Org Chem. 2005 Sep 2;70(18):7232-7
references: 16122242