A new method for generation of non-stabilized α-amino-substituted carbanions by the reaction of magnesium carbenoids with N-lithio arylamines: their reactivity and a new synthesis of α-amino acid derivatives

Autor:	Atsushi Osawa, Atsushi Kondo, Tohru Ohbayashi, Tsuyoshi Satoh
Rok vydání:	2006
Předmět:	Olefin fiber Magnesium Aryl Organic Chemistry chemistry.chemical_element Biochemistry chemistry.chemical_compound chemistry Drug Discovery Electrophile Organic chemistry Ethyl chloroformate Reactivity (chemistry) Carbenoid Carbanion
Zdroj:	Tetrahedron. 62:7892-7901
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.05.052
Popis:	Magnesium carbenoids were generated from aryl 1-chloroalkyl sulfoxides with i-PrMgCl in THF at low temperature in quantitative yields. The magnesium carbenoids were found to be reactive with N-lithio alkylamines to afford an olefin, which was derived from dimerization of the magnesium carbenoid, in moderate yield. On the other hand, reaction of the magnesium carbenoids with N-substituted N-lithio arylamines gave non-stabilized α-amino-substituted carbanions in good yields. Reactivity of the α-amino-substituted carbanions with some electrophiles was investigated and it was found that ethyl chloroformate reacted to give α-amino acid derivatives in good yields. As a whole, a new method for one-pot, three-component combined synthesis of α-amino acid derivatives from aryl 1-chloroalkyl sulfoxides was realized.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b5b8b12efe1c61254f03fc0c5f18e17e https://doi.org/10.1016/j.tet.2006.05.052 Zobrazit plný text záznamu Full Text from ScienceDirect