10.1021/ol5028128.s002
Joseph
J. Badillo
Joseph
J.
Badillo
Carlos J. A. Ribeiro
Carlos
J. A. Ribeiro
Marilyn M. Olmstead
Marilyn M.
Olmstead
Annaliese K. Franz
Annaliese K.
Franz
Titanium(IV)-Catalyzed Stereoselective Synthesis of
Spirooxindole-1-pyrrolines
American Chemical Society
2015
stereoselective
Spirooxindole
diastereoselectivity
pyrroline
alkylidene oxindoles
enantioenriched
spiro
cyclization
methodology
coumarin derivatives
spirooxindole
chloride
Synthesi
reversal
mol
scandium
methoxyoxazole
chiral
Stereoselective
malonate alkylidene
synthesis
2015-12-17 06:31:52
Dataset
https://acs.figshare.com/articles/dataset/Titanium_IV_Catalyzed_Stereoselective_Synthesis_of_Spirooxindole_1_pyrrolines/2045952
A stereoselective
cyclization between alkylidene oxindoles and
5-methoxyoxazoles has been developed using catalytic titanium(IV)
chloride (as low as 5 mol %) to afford spiro[3,3′-oxindole-1-pyrrolines]
in excellent yield (up to 99%) and diastereoselectivity (up to 99:1).
Using a chiral scandium(III)–indapybox/BArF complex affords
enantioenriched spirooxindole-1-pyrrolines where a ligand-induced
reversal of diastereoselectivity is observed. This methodology is
further demonstrated for the synthesis of pyrrolines from malonate
alkylidene and coumarin derivatives.