Synthesis of Functionalized Isoindolinones: Addition of In Situ Generated Organoalanes to Acyliminium Ions.
Addition of in situ generated di- or trisubstituted alkenylalanes to N-acyliminium ions provides rapid access to functionalized isoindolinones. Subsequent ring closing metathesis leads to tricyclic products. These transformations proceed under mild conditions and allow for the convergent synthesis of biologically significant scaffolds from readily available starting materials.
Pierce
Joshua G
JG
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, U.S.A.
Waller
David L
DL
Wipf
Peter
P
Org Biomol Chem. 2005 Jan 7;3(1):31-5
15602595
Org Lett. 2006 Jul 20;8(15):3375-8
16836409
Org Lett. 2003 Sep 18;5(19):3523-5
12967315
Org Lett. 2005 Jan 6;7(1):95-8
15624986
Org Lett. 2005 Jul 7;7(14):2825-8
15987146
Org Lett. 2005 Feb 3;7(3):483-5
15673270
J Org Chem. 2005 Feb 18;70(4):1432-7
15704980
J Med Chem. 1998 Jan 15;41(2):157-66
9457239
J Org Chem. 2000 Mar 10;65(5):1467-74
10814111
Chem Rev. 2004 Mar;104(3):1431-628
15008627
J Org Chem. 2000 Dec 29;65(26):9249-51
11149882
J Org Chem. 2003 Nov 14;68(23):8867-78
14604356
Angew Chem Int Ed Engl. 2000 Sep 1;39(17):3012-3043
11028025
J Org Chem. 2005 Sep 30;70(20):8096-102
16277333
J Med Chem. 1996 Jan 5;39(1):149-57
8568802
Org Biomol Chem. 2004 Feb 21;2(4):443-5
14770219
Org Lett. 2005 Mar 3;7(5):775-8
15727438
Org Lett. 2006 Aug 31;8(18):4101-4
16928084