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

✍ Scribed by Prabhat Arya; Robert N. Ben; Huiping Qin

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 206 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01295-7

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✦ Synopsis

A high diastereoselectivity (98%) for electrophilic amination of compound 9 using di-r-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 a-galactosyl moiety, responsible for inducing the induction from the remote site.

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