Synthesis of an optically pure 3-unsubstituted β-lactam using an asymmetric Reformatsky reaction and its conversion to cholesterol absorption inhibitors

Autor:	Ashit K. Ganguly, Stuart W. McCombie, Kirkup Michael P, John W. Clader, Bandarpalle B. Shankar
Rok vydání:	1996
Předmět:	chemistry.chemical_compound Chemistry Organic Chemistry Drug Discovery Lactam Organic chemistry Reformatsky reaction Menthol Biochemistry Asymmetric induction Cholesterol absorption
Zdroj:	Tetrahedron Letters. 37:4095-4098
ISSN:	0040-4039
Popis:	Asymmetric induction by several chiral alcohols in the reaction of their bromoaceates with imines in the presence of activated Zn (Reformatsky reaction) was studied. Trans -2-phenylcyclohexanol and phenyl menthol gave β-lactam 9 , obtained by cyclizing the diastereoisomeric β-aminoesters 8 , in > 99%ee. The resulting chiral 3-unsubstituted azetidin-2-one 9 was converted to 3-substituted products 11, 12 , and 13 which exhibit cholesterol absorption inhibitory activity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ed96a0211903eb9cba015891fedc0674 https://doi.org/10.1016/0040-4039(96)00764-2 Zobrazit plný text záznamu Full Text from ScienceDirect