Stereocontrolled Route to Vicinal Diamines by [3.3] Sigmatropic Rearrangement of Allyl Cyanate: Asymmetric Synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-Diaminobutanoic Acids

Abstract

A stereocontrolled route via allyl 1,2-diols to vicinal diamines based on the [3.3] sigmatropic rearrangement of allyl cyanate has been developed. Our approach consists of two consecutive steps: stereoselective construction of allyl anti- and syn-1,2-diols followed by [1,3]-chirality transfer by sigmatropic rearrangement, which allow an access to anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids. [reaction: see text]