Straightforward and direct access to β-seleno- amines and sulfonylamides via the controlled addition of phenylselenomethyllithium (LiCH2SePh) to imines

Autor:	Wolfgang Holzer, Vittorio Pace, Raffaele Senatore, Simona Collina, Roberta Listro, Saad Touqeer, Monika Malik
Rok vydání:	2020
Předmět:	Nucleophile 010405 organic chemistry Chemistry Organic Chemistry Drug Discovery 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Carbanion
Zdroj:	Tetrahedron. 76:131220
ISSN:	0040-4020
DOI:	10.1016/j.tet.2020.131220
Popis:	The transfer of a α-methyl phenylseleno carbanion to variously functionalized N-aryl and N-sulfonyl imines is reported. The fast selenium-lithium exchange conducted on a diselenoacetal with n-BuLi enables the generation of the attacking homologative nucleophile under chemoselective conditions preserving concomitant potentially sensitive functionalities to the lithiating conditions. Uniformly high yields were observed, thus establishing a valuable and conceptually simple approach to the title compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e0ed0a110b3eda176dd79f6f0ddc747a https://doi.org/10.1016/j.tet.2020.131220 Zobrazit plný text záznamu Full Text from ScienceDirect