Synthesis of ( Z )‐β‐(Carbonylamino)alkenylindium through Regioselective anti ‐Carboindation of Ynamides and Its Transformation to Multisubstituted Enamides

Autor:	Yoshihiro Nishimoto, Makoto Yasuda, Kyoungmin Kang, Kosuke Sakamoto
Rok vydání:	2020
Předmět:	Silylation 010405 organic chemistry Organic Chemistry Ketene Halogenation Regioselectivity General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Carbometalation chemistry.chemical_compound Nucleophile chemistry Lewis acids and bases
Zdroj:	Chemistry – A European Journal. 26:4930-4934
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201905175
Popis:	The regioselective anti-carboindation of ynamides by using InBr3 and silylated nucleophiles was developed to synthesize (Z)-β-(carbonylamino)alkenylindiums. The X-ray crystallographic analysis of an alkenylindium suggested that the reaction proceeded in an anti-addition fashion. In contrast to reported syn-carbometalations of ynamides by using organometallics, a cooperation of InBr3 and silylated nucleophiles to ynamides achieved an anti-addition, which was supported by DFT calculations. The scope of substrates included various ynamides and silylated nucleophiles, such as silyl ketene acetals and silyl ketene imines. The transformation of synthesized alkenylindiums by iodination, radical coupling, and Pd-catalyzed cross-coupling successfully afforded trisubstituted enamines with high regio- and stereoselectivities.
Databáze:	OpenAIRE
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