Chiral aminal templates 3 diastereoselectivity of organometallic attack on aldehydes bearing a chiral imidazolidine group

Autor:	Pierre Mangeney, R. Sedrani, Jean F. Normant, Alexandre Alexakis
Rok vydání:	1990
Předmět:	Steric effects Organic Chemistry Diastereomer Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound Hydrolysis chemistry Imidazolidine Reagent ddc:540 Aminal Organic chemistry Moiety Chelation Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry, Vol. 1, No 5 (1990) pp. 283-286
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(00)86314-4
Popis:	Monoprotected phthalaldehydes 3 and 4, bearing a chiral imidazolidine auxiliary were reacted with various organometallic reagents. Lithium organocuprates gave almost exclusively one diastereomer whereas an organomanganese reagent gave the opposite one. Hydrolysis of the aminal moiety affords the enantiomerically pure lactols 7a–d. In both 3 and 4 the chiral imidazolidine auxiliary is very effective, but affords opposite results which are rationalized by chelation and/or steric factors.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b1fcb08d31e8619873f728cece6e2e7b https://doi.org/10.1016/s0957-4166(00)86314-4 Zobrazit plný text záznamu