title: Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.
abstract: Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.
authors: Department of Chemistry, University of Puerto Rico-Humacao, Call Box 860, Humacao 00792, Puerto Rico.
authors: Wenhua
authors: W
authors: Ou
authors: Sandraliz
authors: S
authors: Espinosa
authors: Héctor J
authors: HJ
authors: Meléndez
authors: Silvia M
authors: SM
authors: Farré
authors: Jaime L
authors: JL
authors: Alvarez
authors: Valerie
authors: V
authors: Torres
authors: Ileanne
authors: I
authors: Martínez
authors: Kiara M
authors: KM
authors: Santiago
authors: Margarita
authors: M
authors: Ortiz-Marciales
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D057966:Calcimimetic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001881:Borates; D057966:Calcimimetic Agents; D010091:Oximes; D013141:Spiro Compounds
references: J Am Chem Soc. 2005 Dec 21;127(50):17620-1
references: 16351088
references: Pharmacol Ther. 2006 Mar;109(3):339-65
references: 16102839
references: J Org Chem. 2008 Jan 18;73(2):745-8
references: 18154349
references: Chemistry. 2000 May 15;6(10):1840-6
references: 10845644
references: Angew Chem Int Ed Engl. 2010 May 10;49(21):3627-30
references: 20379986
references: Proc Natl Acad Sci U S A. 1998 Mar 31;95(7):4040-5
references: 9520489
references: Diabetes Care. 2000 Mar;23(3):405-11
references: 10868872
references: J Med Chem. 2009 Jul 9;52(13):3982-93
references: 19492813
references: Nephrol Dial Transplant. 2005 Jul;20(7):1315-9
references: 15941845
references: J Ren Nutr. 2006 Jul;16(3):253-8
references: 16825031
references: Curr Med Chem. 2007;14(28):3027-34
references: 18220738
references: Chem Rev. 2003 Aug;103(8):2985-3012
references: 12914489
references: J Am Chem Soc. 2012 Jan 25;134(3):1754-69
references: 22192064
references: J Org Chem. 2000 Sep 8;65(18):5879-81
references: 10970344
references: J Med Chem. 2009 Nov 12;52(21):6535-8
references: 19835382
references: Org Lett. 1999 Jul 29;1(2):293-4
references: 10822565
references: Chemistry. 2011 Dec 9;17(50):13978-82
references: 22105764
references: J Phys Chem A. 2007 Dec 20;111(50):13112-25
references: 18034467
references: Bioorg Med Chem Lett. 2004 Jun 21;14(12):3345-9
references: 15149704
references: Biochemistry. 1998 Dec 8;37(49):17179-91
references: 9860831
references: Chem Commun (Camb). 2010 Aug 21;46(31):5808-10
references: 20593086
references: J Org Chem. 2010 Sep 17;75(18):6271-4
references: 20718448
references: J Med Chem. 2006 Aug 24;49(17):5119-28
references: 16913701
references: Org Lett. 2007 Apr 26;9(9):1793-5
references: 17397177
references: Organic Synth. 2010 Jan 1;87:36-52
references: 20526458
references: J Org Chem. 2008 Sep 5;73(17):6928-31
references: 18690744
references: Org Lett. 2011 Aug 19;13(16):4348-51
references: 21766831
references: J Pharmacol Sci. 2005 Mar;97(3):355-60
references: 15781990
references: J Nephrol. 2011 Jan-Feb;24(1):78-82
references: 20437396
references: Org Lett. 2009 Mar 5;11(5):1075-8
references: 19199770
references: J Org Chem. 2003 May 2;68(9):3546-51
references: 12713358
references: J Org Chem. 2007 May 11;72(10):3729-34
references: 17444684
references: J Org Chem. 2006 May 12;71(10):3998-4001
references: 16674084
references: Molecules. 2012 Feb 24;17(3):2271-82
references: 22367023
references: J Am Chem Soc. 2003 Nov 26;125(47):14260-1
references: 14624558
references: J Org Chem. 2009 Dec 18;74(24):9359-64
references: 19894732
references: Acc Chem Res. 2008 Jul;41(7):831-40
references: 18533688
references: J Org Chem. 2008 Jun 6;73(11):4017-26
references: 18447392
references: J Org Chem. 2008 Jun 6;73(11):4302-4
references: 18454550
references: J Org Chem. 2007 Jan 19;72(2):626-9
references: 17221983
references: Expert Opin Investig Drugs. 2003 Aug;12(8):1413-21
references: 12882626
references: Nature. 1993 Dec 9;366(6455):575-80
references: 8255296
references: Bioorg Med Chem Lett. 2000 Sep 4;10(17):2001-4
references: 10987436
references: J Agric Food Chem. 1980 May-Jun;28(3):673-5
references: 7391411
references: Org Lett. 2011 Nov 4;13(21):5920-3
references: 21995717
references: J Med Chem. 2007 Jul 26;50(15):3528-39
references: 17585751
references: Angew Chem Int Ed Engl. 2002 Jul 2;41(13):2348-50
references: 12203588
references: Org Lett. 2007 Mar 15;9(6):1157-9
references: 17291005
references: Physiol Rev. 1991 Apr;71(2):371-411
references: 2006218
references: J Org Chem. 2009 Aug 7;74(15):5304-10
references: 19555095
references: Angew Chem Int Ed Engl. 2002 Dec 16;41(24):4708-11
references: 12481334
references: J Org Chem. 2008 May 2;73(9):3508-15
references: 18351744
references: Chem Commun (Camb). 2010 Aug 14;46(30):5500-2
references: 20461261
references: Chem Rev. 1999 May 12;99(5):1069-94
references: 11749440
references: Org Lett. 2006 Mar 30;8(7):1359-62
references: 16562891
references: J Am Chem Soc. 2005 Aug 17;127(32):11240-1
references: 16089442