Fluorine-induced diastereodivergence discovered in an equally rare enantioselective syn-aza-Henry reaction.

ABSTRACT: Attention to the aza-Henry reaction, particularly over the past two decades, has resulted in a wide range of effective catalysts for the enantio- and diastereoselective versions, driven by the versatility of the β-amino nitroalkane products as precursors to secondary amines and vic-diamines. Despite this broad effort, syn-diastereoselective variants are exceedingly rare. We have discovered a subset of α-fluoro nitroalkane additions that are characterized by an unusual crossover in diastereoselection, often delivering the products with high selectivities. We report here a rigorous comparative analysis of non-fluorinated and α-fluoro nitroalkanes in their additions to azomethines. Both homogeneous and heterogeneous catalysis were applied to probe the possibility that this pheno

SUBMITTER: Bing JA 

PROVIDER: S-EPMC8890141 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature