Acetoxyl group directed cyclization promoted by SmI2: directing group determined stereocomplementarity

Autor:	Hiroaki Tamiya, Haruhisa Shirahama, Seijiro Hosokawa, Shinji Nara, Toshiyuki Kan, Fuyuhiko Matsuda
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Ketone chemistry Aldol reaction Stereochemistry Group (periodic table) Organic Chemistry Catalyst selectivity Aldehyde Catalysis
Zdroj:	The Journal of organic chemistry. 69(25)
ISSN:	0022-3263
Popis:	Complete reversal of diastereoselectivity was observed in the SmI(2)-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI(2)-induced ketyl-olefin coupling cyclizations of the delta-hydroxy ketone 1 and delta-acetoxy ketone 3.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::291fb5aa01161ab851c5711472becf6d https://pubmed.ncbi.nlm.nih.gov/15575783 Zobrazit plný text záznamu