SYNTHESIS OF (S)-BETA,BETA,BETA-TRIFLUOROLACTIC ACID AND (S)-ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)PHENYLACETIC ACID FROM (R)-METHYL PARA-TOLYL SULFOXIDE

Selectively fluorinated organic compounds are finding increasing applications in several fields.1 Fluorinated substances most commonly employed in analytical,2 bio-logical,3and medicinal chemistry4contain a single fluorine aReagent and conditions: (a) LDA, THF, −78 °C; (b) NaBH4f, MeOH, NH4fOH, −40 °C; (c) NaH, BnBr DMF, 0 °C; (d) (CF3fC-O)2fO, 2,4,6-trimethylpyridine, acetonitrile, 0 °C; (e) HgCl2f, H2fO, room temperature; (f) NaC1O2f, KH2fPO4f, tert-butyl alcohol, 2-methyl-2-butene; (g) CH2fN2f, Et2f0, room temperature. © 1990, American Chemical Society. All rights reserved.