TY - JOUR
T1 - Highly diastereoselective nucleophilic additions using a novel myrtenal-derived oxathiane as a chiral auxiliary
AU - Martínez-Ramos, Federico
AU - Vargas-Díaz, María Elena
AU - Chacón-García, Luis
AU - Tamariz, Joaquín
AU - Joseph-Nathan, Pedro
AU - Zepeda, L. Gerardo
N1 - Funding Information:
The authors wish to thank IQ Fernando Labarrios for MS measurements, and Gabriela Vargas-Diaz and Herbert Höpfl (CIQ, Universidad Autónoma del Estado de Morelos) for providing us the X-ray structure of compound 12 . L.G.Z. acknowledges DEPI/IPN (grant 933503) and CONACyT (grants 1569P and 35013E). L.C.-G. and M.E.V.-D. thank CONACyT (grants 92069 and 125225, respectively) and DEPI/IPN (PIFI) postgraduate fellowships.
PY - 2001/12/10
Y1 - 2001/12/10
N2 - The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (-)-myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected α-hydroxycarbonyl compounds in excellent enantiomeric excess.
AB - The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (-)-myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected α-hydroxycarbonyl compounds in excellent enantiomeric excess.
UR - http://www.scopus.com/inward/record.url?scp=0035842882&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(01)00545-6
DO - 10.1016/S0957-4166(01)00545-6
M3 - Artículo
SN - 0957-4166
VL - 12
SP - 3095
EP - 3103
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 22
ER -