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Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions
Author(s) -
Díaz Buezo Nuria,
de la Rosa Juan Carlos,
Priego Julián,
Alonso Inés,
Carretero Juan Carlos
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010917)7:18<3890::aid-chem3890>3.0.co;2-y
Subject(s) - intermolecular force , heck reaction , chemistry , computational chemistry , organic chemistry , palladium , catalysis , molecule
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 ]/Ag 2 CO 3 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.