TY - JOUR
T1 - First synthesis of the chiral mixed O/S ligands, 1,2-sulfinyl thiols
T2 - Application as chiral proton sources in enantioselective protonations of enolates
AU - Asensio, Gregorio
AU - Gavia, Pablo
AU - Cuenca, Ana
AU - De Arellano, M. Carmen Ramírez
AU - Domingo, Luis R.
AU - Medio-Simón, Mercedes
N1 - Funding Information:
We thank the Dirección General de Enseñanza Superior (PB96-0757) and the Generalitat Valenciana (GVDOC99-22-2) for financial support. Additional thanks go to the Generalitat Valenciana for a grant (A.C.).
PY - 2000/9/8
Y1 - 2000/9/8
N2 - A suitable method for the preparation of the chiral mixed O/S ligands 1,2-sulfinyl thiols is described. These compounds have then been used as a chiral proton source in the enantioselective protonation of 2-methyl tetralone enolate and the results are compared with those obtained from the analogous alcohols. A theoretical model is proposed to explain the different behaviors exhibited in the protonation reaction for each of these proton sources. Configurational assignments for the new chiral thiols have been carried out by means of X-ray analysis. Copyright (C) 2000 Elsevier Science Ltd.
AB - A suitable method for the preparation of the chiral mixed O/S ligands 1,2-sulfinyl thiols is described. These compounds have then been used as a chiral proton source in the enantioselective protonation of 2-methyl tetralone enolate and the results are compared with those obtained from the analogous alcohols. A theoretical model is proposed to explain the different behaviors exhibited in the protonation reaction for each of these proton sources. Configurational assignments for the new chiral thiols have been carried out by means of X-ray analysis. Copyright (C) 2000 Elsevier Science Ltd.
KW - Alpha-sulfinyl alcohols
KW - Beta-hydroxy sulfoxides
KW - Pm3-mo calculations
KW - Ab-initio
KW - Parameters
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U2 - 10.1016/S0957-4166(00)00330-X
DO - 10.1016/S0957-4166(00)00330-X
M3 - Article
AN - SCOPUS:0034622911
SN - 0957-4166
VL - 11
SP - 3481
EP - 3493
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 17
ER -