Sulfoxides as stereochemical controllers in intermolecular Heck reactions.
The study of a variety of substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)2]/Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and asymmetric inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating O-(N,N-dimethylamino)phenylsulfinyl group. By final removal of the chiral auxiliary, these sulfoxide-stereocontrolled asymmetric Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes.
Díaz Buezo
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N
Departamento de Química Orgánica, facultad de Ciencias, Universidad Autónoma de Madrid, Spain.
de la Rosa
J C
JC
Priego
J
J
Alonso
I
I
Carretero
J C
JC