Carbenoid-Mediated Homologation Tactics for Assembling (Fluorinated) Epoxides and Aziridines

Autor:	Vittorio Pace, Veronica Pillari, Laura Ielo, Margherita Miele, Davide Castiglione
Rok vydání:	2020
Předmět:	Reaction conditions Chemistry Organic Chemistry Carbon skeleton aziridines carbenoids epoxides fluorine homologation Combinatorial chemistry chemistry.chemical_compound Electrophile Organic synthesis Carbenoid
Zdroj:	Synlett. 32:551-560
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0040-1706404
Popis:	Homologation strategies provide highly versatile tools in organic synthesis for the introduction of a CH2 group into a given carbon skeleton. The operation can result in diverse structural motifs by tuning of the reaction conditions and the nature of the homologating agent. In this Account, concisely contextualizing our work with lithium carbenoids (LiCH2X, LiCHXY etc) for homologating carbon-centered electrophiles, we focus on the assembly of three-membered cycles featuring fluorinated substituents. Two illustrative case studies are considered: (1) the development and employment of fluorinated carbenoids en route to rare α-fluoroepoxides and aziridines, and (2) the installation of up to halomethylenic groups on trifluoroimidoylacetyl chlorides (TFAICs) for preparing CF3-containing halo- and halomethylaziridines. Collectively, we demonstrate that the initial homologation event generated by the installation of the carbenoid, upon modulation of the conditions, serves as a tool for creating fluorinated building blocks in a single operation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::96c53e9b821bf17931b734f7db5e327f https://doi.org/10.1055/s-0040-1706404 Zobrazit plný text záznamu