Tetrahedron Asymmetry p. 2065 - 2079 (1998)
Update date:2022-07-30
Topics:
Camps, Pelayo
Perez, Francesc
Soldevilla, Nuria
rac-α-Chlorocarboxylic acids, rac-9a-e, were formally deracemized by reaction of the corresponding acyl chlorides with the chiral auxiliaries (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, (R)- and (S)-4, followed by mild alkaline hydrolysis. The highest o.p. (99%) was obtained in the case of (S)-α-chloropropanoic acid, a known precursor for the synthesis of (R)-α-aryloxypropanoic acid herbicides such as dichlorprop-P, (R)-3a, or mecoprop-P, (R)-3b, which, together with their enantiomers, were also obtained in moderate e.e.s by dynamic kinetic resolution from (αRS,3S)-4,4- dimethyl-2-oxo-l-phenylpyrrolidin-3-yl α-bromopropanoate, (αRS,3S)-6, by reaction with the corresponding phenoxide followed by mild acid hydrolysis.
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Doi:10.1002/ardp.200300778
(2003)Doi:10.1515/znb-1984-1128
(1984)Doi:10.1016/S0040-4039(98)01192-7
(1998)Doi:10.1080/00397919808004875
(1998)Doi:10.1021/ja992818u
(1999)Doi:10.1080/00397919808004457
(1998)