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).

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.

SYNTHETIC OPPORTUNITIES OFFERED BY ANTI ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS - STEREOSELECTIVE REACTIONS AT THE DOUBLE-BOND

A. BERNARDI;C.M.A. GENNARI;C. SCOLASTICO
1985

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).
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/176200
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