132235-44-0Relevant academic research and scientific papers
Preparation and Use of Chloromethyl (-)-Menthyl Ether in the Synthesis of Optically Pure α-Branched α-Amino Nitriles
Shatzmiller, Shimon,Dolithzky, Ben-Zion,Bahar, Eliezer
, p. 375 - 379 (2007/10/02)
The synthesis of optically pure chloromethyl (-)-menthyl ether (2b) and its use in the synthesis of di-(-)-menthyl acetal (-)-menthyl (+)-menthyl acetals are described.The diastereomeric mixed acetals 7a,b and 8a,b are easily obtainable from the nitrones 5 and 6, KCN and 2b.The mixture of diastereomers are separated into the pure components 7a, 7b and 8a, 8b by simple silica gel column chromatography.Hydrolysis of these products (H2O2/Na2CO3, ultrasound) followed by N-O cleavage affords the heterocyclic α-methyl-α-amino amides 11a, 11b and 12a, 12b.These are subsequently hydrolyzed to give the corresponding α-methyl-α-amino acids with S and R configuration, respectively.
