Sc3+-Catalyzed Aldol-Type Additions of N-Benzoylcyclopropanecarboxamides via Iodide-Mediated Ring-Opening: Stereoselective Synthesis of γ-Lactams

Autor:	Masakatsu Shibasaki, Shinji Harada, Sean H. Wiedemann, Hidetoshi Noda, Shigeki Matsunaga
Rok vydání:	2008
Předmět:	chemistry.chemical_classification Lactams Organic Chemistry Iodide Iodides Ring (chemistry) Amides Biochemistry Medicinal chemistry Catalysis Stereocenter chemistry Aldol reaction Yield (chemistry) Stereoselectivity Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 10:1661-1664
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol800401g
Popis:	A new catalytic aldol-type addition of cyclopropanecarboximides to aldehydes via iodide-mediated ring-opening is presented. The reaction was found to be catalyzed at 0 degrees C using either a Sc(OTf)3/NaI system or ScI3. Stereoselective formation of alpha,alpha-disubstituted enolates occurred in situ. gamma-Lactams bearing alpha-carbonyl quaternary stereocenters were obtained in 97-57% yield and dr = 90:10-80:20 after ring closure.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fdead2c542d823ab489ed0067aeb23d3 https://doi.org/10.1021/ol800401g Zobrazit plný text záznamu