ChemInform Abstract: MiPNO, a New Chiral Cyclic Nitrone for Enantioselective Amino Acid Synthesis: The Cycloaddition Approach.

Abstract

MiPNO, a New Chiral Cyclic Nitrone for Enantioselective Amino Acid Synthesis:The Cycloaddition Approach. -Nitrone (IV) is resolved via O-acylation of its hydroxylamine (V) with a chiral amino acid. Both the enantiomerically pure nitrone (IV) and the racemate undergo totally regio-and diastereoselective 1,3-dipolar cycloaddition reactions with a range of alkenes and one alkyne. The nitrone reacts from the less hindered side in an exo mode. The reductive cleavage of the N-O bond of the cycloadducts affords the corresponding amino alcohols. A one-pot conversion of cycloadduct (IXd) into enantiopure N-protected α-amino γ-lactone (XII) is also performed.