Catalytic Asymmetric Darzens and Aza‐Darzens Reactions for the Synthesis of Chiral Epoxides and Aziridines

• Published in: ChemCatChem 2018-11, Vol.10 (22), p.5092-5114
• Main Authors: de los Santos, Jesús M., Ochoa de Retana, Ana M., Martínez de Marigorta, Edorta, Vicario, Javier, Palacios, Francisco
• Format: Article
• Language: English
• Subjects: Asymmetry; aza-Darzens reaction; aziridines; Catalysis; catalytic asymmetric synthesis; Chemical synthesis; Darzens reaction; Enantiomers; epoxides; Natural products; Organic chemistry
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201801026

This review presents an overview on the recent advances in the catalytic enantioselective Darzens and aza‐Darzens reactions for the synthesis of enantiopure three‐membered oxygen and nitrogen containing heterocycles. Since the synthesis of epoxides is the most widely explored, compared to their nitrogen counterparts, particularly true when asymmetric synthesis are considered, in the last decades several methodologies have appeared or improved and are now available for the preparation of aziridines in a highly stereo‐ and enantioselective manner. Catalytic asymmetric Darzens and aza‐Darzens reaction constitute an important tool in modern organic chemistry, as there is an increased interest in bioactive natural products and pharmaceutical agents that contain these skeletons. Chiral epoxides and aziridines: In the last decades several methodologies have appeared or improved and are now available for the preparation of epoxides and aziridines in a highly stereo‐ and enantioselective manner. This review covers the most recent advances related to the catalytic enantioselective Darzens and aza‐Darzens reactions for the synthesis of chiral epoxides and aziridines.