Декарбоксилювальне 1,3-протонне переміщення: нетрадиційна стратегія синтезу біологічно значущих аміносполук

• Datum: 2025
• Hauptverfasser: Wzorek, Alicja, Ono, Taizo, Baecker, Daniel, Zhang, Wei, Soloshonok, Vadim A.
• Format: Artikel
• Sprache: Englisch
• Veröffentlicht: V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2025
• Schlagworte: флуор; 1,3-протонне переміщення; флуоровані аміни та амінокислоти; відновлювальне декарбоксилювання; 2,2-дифенілгліцин
• Online Zugang: https://bioorganica.com.ua/index.php/journal/article/view/102
• Назва журналу: Ukrainica Bioorganica Acta

Dedication: Dedicated with admiration and gratitude to Professor Giuseppe Resnati on his 70th birthday, for his pioneering and enduring contributions to fluorine chemistry and the art of noncovalent bonding. The 1,3-proton shift reaction has emerged as a highly convenient, scalable, and synthetically practical strategy for accessing fluorinated amines and amino acids - structural motifs that play a pivotal role in the design of contemporary pharmaceuticals and agrochemicals. This transformation typically proceeds via a biomimetic reductive amination of fluorinated carbonyl compounds, wherein a benzylamine derivative functions dually as the nitrogen source and as a formal reducing agent. Over the past decade, substantial progress has been achieved in this domain, particularly through the strategic use of 1,3-azaallylic anion intermediates in reactions with a broad array of electrophiles. A notable advancement involves the adoption of 2,2-diphenylglycine as a synthetically advantageous alternative to the conventionally employed diphenylmethylamine. In this review, we underscore the benefits of this modification and examine its application across reactions with diverse electrophilic partners, including aldehydes, imines, and allyl alcohol-derived species, enabling the synthesis of vicinal amino alcohols, vicinal diamines, homoallylamines, and α-methylene-γ-amino acids