title: Asymmetric synthesis of aminochromanes via intramolecular indium-mediated allylation of chiral hydrazones.
abstract: The asymmetric intramolecular indium-mediated cyclization reaction delivers chromanes with excellent diastereoselectivity (68-91% yield, dr >99:1). The reaction was efficient for aryl substrates with both electron-withdrawing and -donating groups. Carboxylic acid additives were found to be necessary for optimal reaction.
authors.affiliation: Department of Chemistry and Molecular Biology, North Dakota State University, Department 2735, P.O. Box 6050, Fargo, North Dakota 58108-6050, usa.
authors.forename: Debasis
authors.initials: D
authors.lastname: Samanta
authors.forename: Robert B
authors.initials: RB
authors.lastname: Kargbo
authors.forename: Gregory R
authors.initials: GR
authors.lastname: Cook
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D002839:Chromans / Q000737:chemistry*; D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D008956:Models, Chemical; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000588:Amines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002264:Carboxylic Acids; D002839:Chromans; D006835:Hydrazones; D011714:Pyrans; D007204:Indium
references.citation: Angew Chem Int Ed Engl. 2001 Dec 3;40(23):4491-4493
references.pmid: 12404456
references.citation: Angew Chem Int Ed Engl. 2003 Oct 27;42(41):5061-3
references.pmid: 14595632
references.citation: Angew Chem Int Ed Engl. 2003 Aug 25;42(33):3943-7
references.pmid: 12949876
references.citation: Chem Rev. 1998 Jun 18;98(4):1407-1438
references.pmid: 11848938
references.citation: Chem Rev. 2002 Nov;102(11):4009-91
references.pmid: 12428984
references.citation: J Org Chem. 2007 Aug 31;72(18):6735-41
references.pmid: 17685653
references.citation: Org Lett. 2004 Dec 23;6(26):4825-8
references.pmid: 15606076
references.citation: Org Lett. 2004 May 27;6(11):1741-3
references.pmid: 15151403
references.citation: J Am Chem Soc. 2001 Oct 10;123(40):9922-3
references.pmid: 11583567
references.citation: Tetrahedron. 2007 Sep 17;63(38):9373-9381
references.pmid: 18797497
references.citation: J Org Chem. 2002 Jun 14;67(12):4376-9
references.pmid: 12054979
references.citation: Org Lett. 2002 Aug 22;4(17):2993-5
references.pmid: 12182607
references.citation: Org Lett. 2006 Mar 16;8(6):1045-8
references.pmid: 16524264
references.citation: J Med Chem. 1997 Jan 3;40(1):24-34
references.pmid: 9016325
references.citation: Chem Rev. 2004 Mar;104(3):1431-628
references.pmid: 15008627
references.citation: Angew Chem Int Ed Engl. 2004 Dec 27;44(2):257-9
references.pmid: 15565667
references.citation: J Am Chem Soc. 2002 May 22;124(20):5640-1
references.pmid: 12010028
references.citation: J Org Chem. 2004 Jul 9;69(14):4792-6
references.pmid: 15230604
references.citation: J Org Chem. 2002 May 17;67(10):3317-22
references.pmid: 12003541
references.citation: J Org Chem. 2001 Aug 10;66(16):5624-6
references.pmid: 11485495
references.citation: Angew Chem Int Ed Engl. 2000 Nov 17;39(22):4114-4116
references.pmid: 11093224
references.citation: J Org Chem. 2002 Jun 14;67(12):4352-61
references.pmid: 12054974
references.citation: Chem Rev. 2002 Aug;102(8):2751-72
references.pmid: 12175267
references.citation: Acc Chem Res. 2002 Nov;35(11):984-95
references.pmid: 12437323
references.citation: J Org Chem. 2002 Jul 26;67(15):5359-64
references.pmid: 12126428
references.citation: Chem Rev. 1999 May 12;99(5):1069-94
references.pmid: 11749440
references.citation: Acc Chem Res. 2002 Jul;35(7):533-8
references.pmid: 12118992