(R)-alpha-sulphonyloxy-nitriles, useful for stereospecific synthesis - obtd. by reaction of corresp. (R)-alpha-cyanohydrin with sulphonic acid halide or anhydride in inert solvent in presence of organic base

摘要

(R)-alpha-sulphonyl oxynitriles of formula (I) are new. In (I), R1 = 1-20C alkyl, cycloalkyl or aryl; R2 = toluyl, Me, CF3 or F. Also claimed is a process for the prodn. of (I), by reaction of the corresp. (R)-alpha-cyanohydrin of formula R1-CH(OH)(CN) (II) with a cpd. of formula R2-SO2-X (III) (with X = Hal or =OSO2R2) in inert organic solvent and in the presence of an organic base. Pref., solvent is, e.g., CH2Cl2, CHCl3, hexane, toluene, ether, THF, etc., and base is, e.g., pyridine, picoline, lutidine, piperidine, imidazole, Et3N, etc. USE/ADVANTAGE - For the prodn. of (S)-alpha-acyloxynitriles, (S)-alpha-phthaloylaminonitriles, (S)-alpha-azidonitriles and (S)-aziridines. The invention extends the synthetic potential of optically active cyanohydrins, esp. since the above further reactions of (I) proceed with a high deg. of stereoselectivity to give Walden inversion prods. contg. the original CN gp.