Title:Asymmetric Construction of γ-lactams Displaying All-carbon, Aza-, Thia- and Oxaquaternary
Chiral Centers
Volume: 27
Issue: 15
Author(s): Mario Orena*Samuele Rinaldi*
Affiliation:
- Department D3A, Polytechnic University of Marche, Via Brecce Bianche, Ancona I-60131, Italy
- Department Di.S.V.A., Polytechnic
University of Marche, Via Brecce Bianche, Ancona I-60131, Italy
Keywords:
γ-lactams, tetrasubstituted carbon, enantioselectivity, chiral center, internal asymmetric induction, external asymmetric induction.
Abstract: γ-lactams, bearing one or more chiral centers are important scaffolds and widely occur in many natural
and synthetic products of clinical interest, but the synthetic approaches mainly focus on the preparation of
rings that display trisubstituted carbons, whereas only a few examples concern the construction of chiral γ-
lactams that display tetrasubstituted carbon atoms. However, in recent years, the broad potential of these latter
compounds was recognized and deserved high interest, owing to their complex three-dimensional features and
structural rigidity. Thus, several efforts were engaged in the pursuit of new synthetic strategies towards γ-lactam
rings that contain tetrasubstituted carbons that pose a particular challenge, and the present review gathers advances
reported since 2015 about the enantioselective preparation of these molecules, carried out to exploit both
internal and external asymmetric induction.