Recent advances on asymmetric Strecker reactions

Abstract

The Strecker reaction is one of the most attractive methods for the synthesis of α-amino acids and other bioactive compounds including natural products. The asymmetric Strecker reaction represents a simple and efficient method for the synthesis of optically pure α-amino acid derivatives, nucleic acids, various nitrogen and sulfur containing heterocycles and pharmaceuticals. Over the past several decades, considerable effort has been devoted towards the development of asymmetric Strecker reactions. This review provides an overview of recent asymmetric Strecker reactions, from diastereoselective reactions and catalytic enantioselective reactions including chiral catalytic metal systems and chiral organocatalytic systems.

Asymmetric Catalysis Using Chiral Salen–Metal Complexes: Recent Advances

“…This was accomplished by addition of HCN to an imine in the presence of a chiral aluminum−salen complex. 33 Recent advances in this area have been summarized, 34 and the asymmetric Strecker reaction continues to play an important role in the synthesis of both natural and non-natural α-amino acids. C 1 -symmetric oxovanadium complex 57 prepared from phenylalanine catalyzes asymmetric addition of HCN to imines.…”

Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines

“…An attractive strategy to implement carbonyl umpolung reactions is exemplified by the Stetter reaction, in which a catalyst activates a carbonyl compound directly as an acyl nucleophile for a C–C bond-forming reaction with an electrophile (Scheme b). More recently, the power of carbonyl umpolung reactions was tapped for catalytic asymmetric synthesis through the discovery and development of efficient chiral NHC-carbene catalysts for enantioselective Stetter reactions and numerous other asymmetric reactions (Scheme c) . In principle, the development of imine umpolung reactions should also provide an attractive strategy for the development of C–C bond-forming reactions of distinctive bond disconnections, thereby establishing strategically new approaches for the synthesis of nitrogen-containing compounds.…”

Petasis vs. Strecker Amino Acid Synthesis: Convergence, Divergence and Opportunities in Organic Synthesis

“…Its Schiff bases with various carbonyl compounds undergo enantiofacial cyanide addition in high diastereoisomeric ratio [ 43 ]. After separation of the two diastereoisomers, the N -tert-butanesulfinyl group can be conveniently cleaved by simple methanolic HCl treatment to release the corresponding amino acid hydrochloride in high ee ( Scheme 10 ) [ 44 , 45 ].…”