452096-26-3Relevant articles and documents
A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols
Agami, Claude,Couty, Francois,Evano, Gwilherm
, p. 297 - 302 (2007/10/03)
Enantiopure 2-cyano azetidines were prepared in high yields from β-amino alcohols. This synthesis was shown to be general and is based on two important steps: (i) chlorination of a N-cyanomethylated β-amino alcohol and (ii) a 4-exo-trig ring closure through the alkylation of a lithiated α-amino nitrile. The former step is stereoselective when ephedrine-derived β-amino alcohols are used. In the case of a phenylglycinol-derived β-amino alcohol, this step also involves a rearrangement.