title: Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions.
abstract: Four catalysts based on new amides of chiral 1,2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of 4-hydroxycoumarin to enones gives ee's up to 83% and almost quantitative yields in many cases. This novel type of catalysis provides an effective alternative to conventional primary amino catalysis were strong acid additives are essential components.
authors: Department of Chemistry, Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany.
authors: Matthias
authors: M
authors: Leven
authors: Jörg M
authors: JM
authors: Neudörfl
authors: Bernd
authors: B
authors: Goldfuss
keywords: DFT-calculations; Lewis acids; Michael addition; alkali metals; aminocatalysis
references: Clin Pharmacol Ther. 2005 Jun;77(6):479-85
references: 15961979
references: Br J Clin Pharmacol. 1978 Feb;5(2):187-8
references: 619952
references: Chem Asian J. 2010 Mar 1;5(3):422-34
references: 20052703
references: J Med Chem. 2001 Mar 1;44(5):664-71
references: 11262077
references: Org Lett. 2007 Feb 1;9(3):413-5
references: 17249775
references: J Am Chem Soc. 2007 Sep 19;129(37):11336-7
references: 17715928
references: Org Lett. 2011 Aug 19;13(16):4382-5
references: 21770363
references: Chemistry. 2010 Apr 12;16(14):4177-80
references: 20229539
references: Angew Chem Int Ed Engl. 2009;48(24):4349-53
references: 19434637
references: Acc Chem Res. 2004 Aug;37(8):558-69
references: 15311955
references: Org Lett. 2005 Apr 14;7(8):1637-9
references: 15816771
references: Clin Pharmacol Ther. 1978 Feb;23(2):212-7
references: 620483
references: Org Lett. 2007 Nov 22;9(24):5063-6
references: 17958367
references: Angew Chem Int Ed Engl. 2009;48(40):7338-42
references: 19739177
references: Clin Pharmacokinet. 2005;44(12):1227-46
references: 16372822
references: Angew Chem Int Ed Engl. 2003 Oct 20;42(40):4955-7
references: 14579449
references: J Am Chem Soc. 2008 Jul 2;130(26):8134-5
references: 18529055
references: N Engl J Med. 1976 Aug 12;295(7):354-7
references: 934223
references: Chemistry. 2010 Apr 12;16(14):4337-46
references: 20222091
references: Org Lett. 2009 Jun 4;11(11):2249-52
references: 19415906
references: Angew Chem Int Ed Engl. 2008;47(42):8112-5
references: 18814166
references: Chem Commun (Camb). 2008 Dec 14;(46):6242-4
references: 19082133