TY - JOUR
T1 - Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary
AU - Vargas-Díaz, María Elena
AU - Chacón-García, Luis
AU - Velázquez, Pedro
AU - Tamariz, Joaquín
AU - Joseph-Nathan, Pedro
AU - Zepeda, L. Gerardo
N1 - Funding Information:
The authors wish to thank QFB Fernando Labarrios for MS measurements. L.G.Z. acknowledges CGPI/IPN (grant 20020683) and CONACyT (35013E). L.C.-G. and M.E.V.-D. thank CONACyT (grants 92069 and 125225, respectively) and CGPI/IPN (PIFI) postgraduate fellowships. P.V.-P. thanks Institutional Fellowship (CGPI/IPN).
PY - 2003/10/17
Y1 - 2003/10/17
N2 - The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee).
AB - The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee).
UR - http://www.scopus.com/inward/record.url?scp=1242290733&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2003.07.017
DO - 10.1016/j.tetasy.2003.07.017
M3 - Artículo
SN - 0957-4166
VL - 14
SP - 3225
EP - 3232
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 20
ER -