TY - JOUR
T1 - Diastereoselective preparation of (R)- and (S)-2-methoxy-2-phenylpent-3- ynoic acids and their use as reliable chiral derivatizing agents
AU - Pérez-Estrada, Salvador
AU - Joseph-Nathan, Pedro
AU - Jiménez-Vázquez, Hugo A.
AU - Medina-López, Manuel E.
AU - Ayala-Mata, Francisco
AU - Zepeda, L. Gerardo
PY - 2012/2/17
Y1 - 2012/2/17
N2 - Benzoyl-S,O-acetals 1a and 1b were used as chiral auxiliaries to achieve the diastereoselective preparation of both enantiomers of 2-methoxy-2- phenylpent-3-ynoic acids (MPPAs). The latter were condensed with several chiral secondary alcohols and some primary amines to evaluate their potential as chiral derivatizing agents (CDAs). The 1H NMR spectra of the corresponding esters and amides showed strong consistency with the absolute configuration of the carbinol and amine moieties, whose observed ΔδL 1 and ΔδL 2 values were in the ranges of 0.1-0.4 and 0.02-0.12 ppm, respectively.
AB - Benzoyl-S,O-acetals 1a and 1b were used as chiral auxiliaries to achieve the diastereoselective preparation of both enantiomers of 2-methoxy-2- phenylpent-3-ynoic acids (MPPAs). The latter were condensed with several chiral secondary alcohols and some primary amines to evaluate their potential as chiral derivatizing agents (CDAs). The 1H NMR spectra of the corresponding esters and amides showed strong consistency with the absolute configuration of the carbinol and amine moieties, whose observed ΔδL 1 and ΔδL 2 values were in the ranges of 0.1-0.4 and 0.02-0.12 ppm, respectively.
UR - http://www.scopus.com/inward/record.url?scp=84857212927&partnerID=8YFLogxK
U2 - 10.1021/jo2016554
DO - 10.1021/jo2016554
M3 - Artículo
SN - 0022-3263
VL - 77
SP - 1640
EP - 1652
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -