SYNTHETIC OPPORTUNITIES OFFERED BY ANTI ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS - STEREOSELECTIVE REACTIONS AT THE DOUBLE-BOND
Articolo
Data di Pubblicazione:
1985
Citazione:
SYNTHETIC OPPORTUNITIES OFFERED BY ANTI ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS - STEREOSELECTIVE REACTIONS AT THE DOUBLE-BOND / A. BERNARDI, M.G. BERETTA, L. COLOMBO, C.M.A. GENNARI, G. POLI, C. SCOLASTICO. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 50:23(1985), pp. 4442-4447. [10.1021/jo00223a005]
Abstract:
Addition of tert-butyl @-(dimethy1amino)propionate to (S)-0-[( benzyloxy)methyl]lactaldehydea nd (R)-2,3-
0-isopropylideneglyceraldehyde gave, after N-methylation and elimination, a-methylene-@-hydroxy-y-alkoxy
esters in fairly good yield (4040%) and a high anti-syn ratio (7-12:l). These esters were easily lactonized, by
acidic treatment, to the corresponding a-methylene-@-hydroxy-y-butyrolactonesT.h e double bond of these
compounds was submitted to various reactions (cuprate addition, reduction, dihydroxylation). The stereoselectivity
of these reactions was studied and ranged from poor to good depending on the specific substrate and reaction
used. Acyclic substrates proved to be more selective than the corresponding y-lactones. The stereoconfiguration
of the products was assigned by comparison to known compounds (blastmycinolactol-a, epi-D-hamamelose).
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
A. Bernardi, M.G. Beretta, L. Colombo, C.M.A. Gennari, G. Poli, C. Scolastico
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