Studies on d -Glucosamine Derivatives. VIII. 1-C-Substituted-1-anilino-1-deoxy- d -arabitols

In the reaction of 3,4; 5,6-di-O-isopropylidene-N-phenyl-d-glucosaminonitrile and Grignard reagents or alkyl lithiums, the nitrile group was substituted for alkyls to yield each pair of diastereoisomers of the 1-C-substituted-1-ailino-1-deoxy-d-arabitols. The levo-rotating diastereoisomer was, moreover, exclusively predominant in the former case, and the dextro-rotating one in the latter The reaction mechanism for the above asymmetric induction was discussed.