ChemInform Abstract: Development of a Chiral Propionaldehyde Homoenolate Equivalent Which Reacts with Imines with Excellent Stereoselectivity: Efficient and Practical Synthesis of Optically Active γ-Amino Carbonyl Compounds.
Abstract
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ChemInform Abstract
An allyltitanium intermediate formed by reaction of acetal (I) with (η2-propene)Ti(O-iPr)2 reacts with imines such as (II) to give optically active α-addition products (III) predominantly as (E)-enol ethers. Pure (E)-isomers with 96—98% e.e. are isolated from the E/Z product mixtures of (IIIc) and (IIId). The versatility of the enol ether functionality is demonstrated by conversion of derivative (IIIc) into β-amino ester (IV) and γ-amino acid (V).
