ChemInform Abstract: Extremely Stereoselective and Stereospecific Reductive Cleavage of β-Lactams: A Highly Efficient Route to Labelled Homochiral Peptides.
Abstract
Cleavage of β-lactams of type (I) with D2 leads stereospecifically to dipeptide derivatives (II) in quantitative yields.
ChemInform Abstract
Cleavage of β-lactams of type (I) with D2 leads stereospecifically to dipeptide derivatives (II) in quantitative yields. While it is known that the configuration at C-2 is not affected by this Conversion, the situation at C-3 is now elucidated. Using chiral rhodium complexes as catalysts, the required reference compounds (IV) and (VI) are prepared by asym. hydrogenation of (VII) according to established procedures. These diastereomers turn out to be identical with the products obtained from the hydrogenolysis of (III) and (V), resp., thus indicating that the reductive ring opening proceeds with inversion of configuration at C-3 (and, consequent1y, not via an intermediate metallacycle).
