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Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands.

Authors :
Mangunuru, Hari P. R.
Malapit, Christian A.
Haddad, Nizar
Reeves, Jonathan T.
Bo Qu
Rodriguez, Sonia
Heewon Lee
Yee, Nathan K.
Song, Jinhua J.
Busacca, Carl A.
Senanayake, Chris H.
Source :
Synthesis; 2018, Vol. 50 Issue 22, p4435-4443, 9p
Publication Year :
2018

Abstract

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i-Pr-BI-DIME and Me2-BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd<subscript>2</subscript>(dba)<subscript>3</subscript>/i-Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me<subscript>2</subscript>-BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00397881
Volume :
50
Issue :
22
Database :
Complementary Index
Journal :
Synthesis
Publication Type :
Academic Journal
Accession number :
132882579
Full Text :
https://doi.org/10.1055/s-0036-1591590