title: A general, enantioselective synthesis of β- and γ-fluoroamines.
abstract: In this Letter, we describe a short, high yielding protocol for the enantioselective (87-96% ee) and general synthesis of β-fluoroamines and previously difficult to access γ-fluoroamines from commercial aldehydes via organocatalysis.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232, USA.
authors.forename: Matthew C
authors.initials: MC
authors.lastname: O'Reilly
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
keywords: Enantioselective; Organocatalysis; β-fluoroamine; γ-fluoroamine
references.citation: Angew Chem Int Ed Engl. 2004 Oct 18;43(41):5507-10
references.pmid: 15484250
references.citation: J Med Chem. 2001 May 10;44(10):1603-14
references.pmid: 11334570
references.citation: Org Lett. 2012 Jun 1;14(11):2910-3
references.pmid: 22616979
references.citation: J Med Chem. 2008 Jul 10;51(13):3692-5
references.pmid: 18540666
references.citation: Org Lett. 2009 Feb 19;11(4):943-6
references.pmid: 19159275
references.citation: Org Lett. 2010 May 21;12(10):2186-9
references.pmid: 20408600
references.citation: Org Lett. 2010 Jul 16;12(14):3276-8
references.pmid: 20552963
references.citation: J Med Chem. 2008 Oct 23;51(20):6471-7
references.pmid: 18817368
references.citation: J Org Chem. 2012 Apr 20;77(8):4177-83
references.pmid: 22489747
references.citation: Tetrahedron Lett. 2012 Mar 28;53(13):1539-1542
references.pmid: 22919116
references.citation: Org Lett. 2010 Aug 6;12(15):3356-9
references.pmid: 20575576
references.citation: Org Lett. 2011 Oct 21;13(20):5684-7
references.pmid: 21942742
references.citation: Org Lett. 2010 Jul 2;12(13):2936-9
references.pmid: 20509635
references.citation: J Org Chem. 2010 Nov 5;75(21):7365-72
references.pmid: 20931997
references.citation: J Med Chem. 2008 Aug 14;51(15):4359-69
references.pmid: 18570365
references.citation: J Am Chem Soc. 2005 Jun 22;127(24):8826-8
references.pmid: 15954790
references.citation: Chem Soc Rev. 2008 Feb;37(2):320-30
references.pmid: 18197348
references.citation: J Am Chem Soc. 2004 Apr 21;126(15):4790-1
references.pmid: 15080678
references.citation: Chem Soc Rev. 2008 Feb;37(2):308-19
references.pmid: 18197347
references.citation: J Org Chem. 2012 Jan 6;77(1):221-8
references.pmid: 22148510