Sharpless Aminohydroxylation

Abstract

Several protocols have been reported for an osmium‐based enantiomeric transformation of olefins into corresponding α‐amino alcohols with nitrogen bound to a less‐substituted carbon using tert ‐alkyl imido osmium compound as the nitrogen source. Thus any of these procedures to give α‐amino alcohols are referred to as the sharpless aminohydroxylation. This reaction is sensitive towards the temperature and the geometry of olefinic substrate. Various nitrogen sources have been addressed for this reaction, such as chloramines‐T, N ‐chlorosodiocarbamates, and N ‐bromo‐ N ‐lithio salt of primary carboxamidesc and found that the protocol using N ‐chlorosodiocarbamates as the nitrogen source in the presence of silver nitrate offers better regioselectivity. This reaction is useful in organic synthesis for generating chiral vicinal amino alcohols with two functional groups.