On the Synthesis and Reactivity of Enantiopure Azetidines

Abstract

Abstract β‐Amino alcohols with an ( E )‐vinylsilane moiety were cyclized in the presence of N ‐bromosuccinimide to afford diastereomerically pure azetidines. The chemo‐ and stereoselectivities of this bromocyclization are discussed. AM1 calculations support the observed chemoselectivity. The reactivity of the azetidines towards fluorinated reagents was studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)