The tert-butyl sulfoximine group as an effective ortho-director of lithiation: ortho-metallated S-(tert-butyl)-S-phenylsulfoximines

Autor:	B.Langer Eriksen, Mikael Begtrup, G. Dupas, J. Duflos, Jean-Jacques Bourguignon, Vincent Levacher, Guy Quéguiner
Rok vydání:	1999
Předmět:	Benzaldehyde Tert butyl chemistry.chemical_compound chemistry Trimethylsilyl Group (periodic table) Organic Chemistry Drug Discovery Electrophile Organic chemistry Biochemistry Medicinal chemistry
Zdroj:	Tetrahedron Letters. 40:1665-1668
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(99)00060-x
Popis:	The readily available S-(tert-butyl)-N-(trimethylsilyl)-S-phenylsulfoximine was prepared from S-methyl-N-(trimethylsilyl)-S-phenylsulfoximine via lithiation-methylation sequences. The reaction with n-butyllithium in THF at −78°C afforded the corresponding ortho-lithiated species which could be trapped with different electrophiles in good yields. Addition of benzaldehyde proceeded with a modest diastereoselectivity (de=52%).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::80375cd96273665597cdfe0a8299c796 https://doi.org/10.1016/s0040-4039(99)00060-x Zobrazit plný text záznamu Full Text from ScienceDirect