Synthesis of chiral lactams via asymmetric hydrogenation of α,β-unsaturated nitriles?

Organic & Biomolecular Chemistry Pub Date: 2016-03-31 DOI: 10.1039/C6OB00310A

Abstract

A highly efficient Rh-catalyzed enantioselective hydrogenation of α,β-unsaturated nitriles containing ester/amide groups has been developed. Under mild conditions, with a complex of rhodium and (S,S)-f-spiroPhos as the catalyst, a variety of α,β-unsaturated nitriles bearing an ester or amide group were successfully hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.7% ee) and high turnover numbers (TON = 10?000). Furthermore, this catalyst system was also successfully applied to the synthesis of important chiral pharmacophore fragments, lactams, Paroxetine and amino acids.

Graphical abstract: Synthesis of chiral lactams via asymmetric hydrogenation of α,β-unsaturated nitriles
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