High diastereoface selection in an ester enolate addition to. alpha.-alkoxy aldehydes: stereoselective synthesis of. alpha.-methylene-. beta.-hydroxy-. gamma.-alkoxy …

L Banfi, A Bernardi, L Colombo, C Gennari…

Index: Banfi, Luca; Bernardi, Anna; Colombo, Lino; Gennari, Cesare; Scolastico, Carlo Journal of Organic Chemistry, 1984 , vol. 49, # 20 p. 3784 - 3790

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Citation Number: 53

Abstract

For this purpose we synthesized two series of a-alkoxy aldehydes 11-13 and 18-20. 0- Protected lactaldehydes 11-13 were prepared in optically active form15 starting from easily available (-)-@)-ethyl lactate via the O-protected lactates 6-816 (Scheme 111). Esters 6-8 were reduced (LiAlH4) to the alcohols and reoxidized with Collins' reagent1'or directly transformed into the aldehyde using diisobutylaluminium hydride (DIBAH) at low ...