Direct catalytic asymmetric Mannich-type reactions of isomerizable aliphatic imines: chemoselective enolate formation from a hydroxyketone by a Zn-catalyst

Autor:	Akitake Yamaguchi, Shigeki Matsunaga, Masakatsu Shibasaki
Rok vydání:	2006
Předmět:	chemistry Yield (chemistry) Organic Chemistry Drug Discovery Enantioselective synthesis chemistry.chemical_element Organic chemistry Zinc Biochemistry Catalysis
Zdroj:	Tetrahedron Letters. 47:3985-3989
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2006.04.016
Popis:	A direct catalytic asymmetric Mannich-type reaction of isomerizable aliphatic imines is described. A Et2Zn/(S,S)-linked-BINOL complex was suitable for chemoselective enolate formation from a hydroxyketone in the presence of isomerizable aliphatic N-diphenylphosphinoyl imines. The reaction proceeds smoothly and β-alkyl-β-amino-α-hydroxyketones were obtained in good yield and high enantioselectivity (up to 99% ee), albeit in modest to low diastereoselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3b407767475bd99242a9872a3c0ccf47 https://doi.org/10.1016/j.tetlet.2006.04.016 Zobrazit plný text záznamu Full Text from ScienceDirect