Remote asymmtric induction: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination

Article abstract of DOI:10.1016/S0040-4039(98)01295-7

A high diastereoselectivity (98%) for electrophilic of compound 9 using di-t-butyl azodicarboxyl ester as an electrophile was achieved. A similar reaction with compound 13 having achiral oxazolidinone was studied to examine 1,4-remote asymmetric induction. In the latter, a selectivity of 6.5:1 demonstrated the effect of α-galactosyl moiety, responsible for inducing the induction from the remote site.