title: Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.
abstract: The enantioselective α-alkenylation of aldehydes has been accomplished using boronic acids via the synergistic combination of copper and chiral amine catalysis. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of α-formyl olefins employing common building blocks for organic synthesis.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Jason M
authors.initials: JM
authors.lastname: Stevens
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000588:Amines; D001897:Boronic Acids; D003300:Copper
references.citation: J Am Chem Soc. 2008 Mar 19;130(11):3302-3
references.pmid: 18302392
references.citation: J Am Chem Soc. 2008 Jul 2;130(26):8172-4
references.pmid: 18543910
references.citation: Org Lett. 2001 Jun 14;3(12):1897-900
references.pmid: 11405739
references.citation: J Am Chem Soc. 2012 Jul 4;134(26):10773-6
references.pmid: 22712572
references.citation: Organometallics. 2012 Nov 26;31(22):7948-7957
references.pmid: 23204631
references.citation: J Am Chem Soc. 2010 Apr 14;132(14):5010-1
references.pmid: 20302338
references.citation: J Am Chem Soc. 2013 Apr 17;135(15):5557-60
references.pmid: 23540731
references.citation: J Am Chem Soc. 2013 Apr 10;135(14):5332-5
references.pmid: 23521626
references.citation: Chem Sci. 2012 Jan 1;2012(3):633-658
references.pmid: 22518271
references.citation: J Am Chem Soc. 2012 Jun 6;134(22):9090-3
references.pmid: 22616631
references.citation: Chem Sci. 2012;3(1):58-61
references.pmid: 22308217
references.citation: J Am Chem Soc. 2008 Jan 16;130(2):398-9
references.pmid: 18095690
references.citation: J Am Chem Soc. 2012 Jul 4;134(26):10815-8
references.pmid: 22716914
references.citation: Curr Opin Chem Biol. 2005 Jun;9(3):285-92
references.pmid: 15939330
references.citation: Science. 2009 Mar 20;323(5921):1593-7
references.pmid: 19299616
references.citation: Chem Soc Rev. 2009 Sep;38(9):2745-55
references.pmid: 19690751
references.citation: Dalton Trans. 2010 Feb 14;39(6):1423-31
references.pmid: 20104295
references.citation: J Am Chem Soc. 2010 Apr 14;132(14):4986-7
references.pmid: 20297822
references.citation: J Nat Prod. 2013 Apr 26;76(4):600-6
references.pmid: 23806071
references.citation: Org Biomol Chem. 2012 Jan 14;10(2):211-24
references.pmid: 22072256
references.citation: Angew Chem Int Ed Engl. 2006 Oct 6;45(39):6551-4
references.pmid: 16953500
references.citation: Org Lett. 2005 Feb 17;7(4):681-4
references.pmid: 15704924
references.citation: J Nat Prod. 2010 Oct 22;73(10):1706-7
references.pmid: 20886871
references.citation: J Org Chem. 2003 Aug 22;68(17):6583-6
references.pmid: 12919019
references.citation: Angew Chem Int Ed Engl. 2013 May 27;52(22):5799-802
references.pmid: 23610012
references.citation: J Am Chem Soc. 2011 Sep 7;133(35):13778-81
references.pmid: 21848264
references.citation: J Am Chem Soc. 2011 Sep 7;133(35):13782-5
references.pmid: 21848265
references.citation: J Am Chem Soc. 2011 Mar 30;133(12):4260-3
references.pmid: 21388207
references.citation: J Am Chem Soc. 2009 Jul 29;131(29):9900-1
references.pmid: 19580273
references.citation: J Am Chem Soc. 2009 Apr 15;131(14):5044-5
references.pmid: 19309072