A bismuth(III) triflate catalyzed three-component synthesis of α-substituted amides starting from amides, aldehydes, and (hetero)arenes is reported. The reaction has a broad substrate scope, encompassing formaldehyde as well as aryl and alkyl aldehydes. Low catalyst loadings are required, and water is formed as the only side product. The scope and limitation of this method will be discussed.
A highly efficient Bi(OTf)3-catalyzed multicomponent synthesis of arylglycines from readily available starting materials is described. The reaction proceeds under mild conditions and provides a general route to various N-protected arylglycines.
Efficient bismuth-and iron-catalyzed three-component syntheses of α-arylglycines have been developed. These methods provide a general, atom-economic route to various N-protected α-arylglycines starting from readily available amides (or carbamates), glyoxalates, and (hetero)arenes with water as the only by-product. Scope and limitations of bismuth-and iron-catalyzed reactions are discussed and compared. In addition, mechanistic investigations as well as initial forays into stereoselective three-component reactions are presented.
A highly efficient Bi(OTf) 3 -catalyzed multicomponent synthesis of amidomethylated arenes and heteroarenes from readily available starting materials has been developed. This reaction proceeds under mild conditions, has a broad substrate scope, and in addition water is generated as only side product.
An N,O-protected, iodinated bishomoalanine derivative, safely available from glutamic acid, reacts with aryl halides in a Negishi reaction in high yields. From the coupling product, Fmocprotected amino acids with aromatic and heteroaromatic side chains were generated in high yields by racemization-free procedures. These monomers could be used for solid-phase peptide synthesis.
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