TY - JOUR
T1 - New S,O-acetals from (1R)-(-)-myrtenal as chiral auxiliaries in nucleophilic additions
AU - Chacón-García, Luis
AU - Lagunas-Rivera, Selene
AU - Pérez-Estrada, Salvador
AU - Vargas-Díaz, M. Elena
AU - Joseph-Nathan, Pedro
AU - Tamariz, Joaquín
AU - Zepeda, L. Gerardo
N1 - Funding Information:
This work was supported by CONACyT (grant 35013E) and CGPI-IPN (grant 20030702). L.C.-G., M.E.V.-D. and S.L.-R. thank CONACyT (92069, 125225 and 165282, respectively) and CGPI/IPN (PIFI) postgraduate fellowships. S.P.-E. acknowledges CGPI/IPN (PIFI) for undergraduate fellowship.
PY - 2004/3/1
Y1 - 2004/3/1
N2 - Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99% yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er).
AB - Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99% yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er).
KW - (1R)-(-)-Myrtenal
KW - Chiral 1,2-diols
KW - Diastereoselective nucleophilic additions
KW - S,O-acetals
UR - http://www.scopus.com/inward/record.url?scp=1242317873&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2004.01.046
DO - 10.1016/j.tetlet.2004.01.046
M3 - Artículo
SN - 0040-4039
VL - 45
SP - 2141
EP - 2145
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 10
ER -