Stereoelectronic control in the reductive opening of cyclopropylogous α-haloketones

Autor:	Hans-Jürg Borschberg, Eduard J. Brunner, René Beerli
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Reaction mechanism Bicyclic molecule Reducing agent Chemistry Organic Chemistry Cyclohexanone Biochemistry Haloketone chemistry.chemical_compound Drug Discovery Chemical reduction Organic chemistry Bond cleavage
Zdroj:	Tetrahedron Letters. 33:6449-6452
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)79012-5
Popis:	Each of the two epimeric cyclopropylogous α-bromoketones 4 and 5 could be cleaved reductively with high diastereoselectivity to either (E)- or (Z)- 2,2-dimethyl-5-(1-propenyl)cyclohexanone (6 or 7, resp.), depending on the reducing agent employed (SmI2 or NaHTe). Thus, it was demonstrated that both reducing systems bring across the stereochemical information contained in the starting materials, albeit in an opposing and, therefore, complementary sense.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ac94dc333d33d902da62fae962de3e6f https://doi.org/10.1016/s0040-4039(00)79012-5 Zobrazit plný text záznamu