title: Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.
abstract: A diastereo- and enantioselective CuH-catalyzed method for the preparation of highly functionalized indolines is reported. The mild reaction conditions and high degree of functional group compatibility as demonstrated with substrates bearing heterocycles, olefins, and substituted aromatic groups, renders this technique highly valuable for the synthesis of a variety of cis-2,3-disubstituted indolines in high yield and enantioeselectivity.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
authors.forename: Erhad
authors.initials: E
authors.lastname: Ascic
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry
chemical_list: D000447:Aldehydes; D007211:Indoles; D020058:Styrene; C057812:indoline; D003300:Copper
references.citation: J Am Chem Soc. 2003 Jul 23;125(29):8779-89
references.pmid: 12862472
references.citation: Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5821-3
references.pmid: 15067136
references.citation: Angew Chem Int Ed Engl. 2004 Apr 19;43(17):2228-30
references.pmid: 15108129
references.citation: J Am Chem Soc. 2004 Jul 14;126(27):8352-3
references.pmid: 15237972
references.citation: Angew Chem Int Ed Engl. 2005 Feb 18;44(9):1366-8
references.pmid: 15674986
references.citation: J Am Chem Soc. 2003 Sep 17;125(37):11253-8
references.pmid: 16220945
references.citation: J Am Chem Soc. 2006 Nov 8;128(44):14264-5
references.pmid: 17076493
references.citation: Acc Chem Res. 2007 Feb;40(2):151-61
references.pmid: 17309195
references.citation: Chem Rev. 2008 Aug;108(8):2916-27
references.pmid: 18616323
references.citation: J Comb Chem. 2009 Mar 9;11(2):303-9
references.pmid: 19146410
references.citation: J Am Chem Soc. 2009 Mar 11;131(9):3160-1
references.pmid: 19256564
references.citation: J Am Chem Soc. 2009 Jul 8;131(26):9432-41
references.pmid: 19527024
references.citation: Angew Chem Int Ed Engl. 2009;48(33):6062-4
references.pmid: 19591178
references.citation: J Am Chem Soc. 2009 Aug 5;131(30):10386-7
references.pmid: 19722617
references.citation: J Am Chem Soc. 2010 Jul 7;132(26):8909-11
references.pmid: 20552968
references.citation: Acc Chem Res. 2011 Jun 21;44(6):447-57
references.pmid: 21491859
references.citation: J Am Chem Soc. 2011 May 25;133(20):7859-71
references.pmid: 21526827
references.citation: Chemistry. 2011 Jun 20;17(26):7193-7
references.pmid: 21567504
references.citation: Angew Chem Int Ed Engl. 2011 Nov 4;50(45):10661-4
references.pmid: 21932274
references.citation: J Org Chem. 2012 Jan 6;77(1):808-12
references.pmid: 22148595
references.citation: Org Biomol Chem. 2012 Feb 14;10(6):1235-8
references.pmid: 22179620
references.citation: Angew Chem Int Ed Engl. 2012 Feb 27;51(9):2238-42
references.pmid: 22308174
references.citation: J Org Chem. 2012 Sep 21;77(18):8049-55
references.pmid: 22917174
references.citation: J Am Chem Soc. 2012 Oct 3;134(39):16131-4
references.pmid: 22985198
references.citation: J Med Chem. 2013 Feb 14;56(3):625-7
references.pmid: 23316748
references.citation: Org Lett. 2013 Mar 1;15(5):1112-5
references.pmid: 23427913
references.citation: J Am Chem Soc. 2013 Apr 3;135(13):4934-7
references.pmid: 23495912
references.citation: J Am Chem Soc. 2013 Aug 14;135(32):11740-3
references.pmid: 23865933
references.citation: Proc Natl Acad Sci U S A. 2013 Sep 24;110(39):15573-8
references.pmid: 24019472
references.citation: Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10830-4
references.pmid: 24038866
references.citation: J Am Chem Soc. 2013 Oct 23;135(42):15746-9
references.pmid: 24106781
references.citation: Angew Chem Int Ed Engl. 2014 Feb 17;53(8):2034-6
references.pmid: 24470434
references.citation: J Med Chem. 2014 Feb 27;57(4):1488-94
references.pmid: 24491146
references.citation: J Am Chem Soc. 2014 May 28;136(21):7688-700
references.pmid: 24833267
references.citation: J Am Chem Soc. 2014 Nov 12;136(45):15913-6
references.pmid: 25339089
references.citation: Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1638-41
references.pmid: 25475991
references.citation: Nat Chem. 2015 Jan;7(1):38-44
references.pmid: 25515888
references.citation: Angew Chem Int Ed Engl. 1998 May 4;37(8):1103-1107
references.pmid: 29711023
references.citation: J Pharm Biomed Anal. 1994 Oct;12(10):1283-7
references.pmid: 7841224
references.citation: Med Res Rev. 1995 Jan;15(1):3-31
references.pmid: 7898167