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An efficient methodology for the enantioselective synthesis of γ-lactams, using a one-pot reaction of chiral N-alkoxycarbonyl γ-amino α,β-unsaturated carboxylates with magnesium in methanol, afforded the target chiral compounds in high chemical yield (87–95%) and optical purity (96–99% ee).

The α-ester group of N-protected diethyl aspartate ( 1a ) or diethyl glutamate ( 1b ) was selectively reduced using diisobutylaluminum hydride (DIBALH) in the presence of a lithium trialkylphosphonoacetate ( 2 ) to afford N-protected γ-amino-α,β-unsaturated dicarboxylates ( 4 ).

Magnesium methoxide is a simple, effective and highly selective reagent for the deprotection of N-alkoxycarbonyl lactams. The cleavage occurs via six-membered ring transition states involving coordination of magnesium ion with the oxygens of the carbamate and lactam carbonyl groups.

(1994). RESOLUTION OF 5-VINYL-2-PYRROLIDINONE. A PRACTICAL SYNTHESIS OF (S)- AND (R)-VIGABATRIN. Organic Preparations and Procedures International: Vol. 26, No. 5, pp. 567-570.

Directed crossed aldol type condensations can be carried out in aqueous media using α-halocarbonyl compounds, aldehydes, and metallic zinc or tin.

La condensation d'ethers d'alkyle et d'allyldimethylsilyle avec des aldehydes conduit a des alcools homoallyliques (alcene-1ols-3) et a des dialkyl-2,6 tetrahydropyrannes

The condensation of alkoxyallylsilanes with carbonyl compounds under Lewis acid conditions gave all cis -4-chloro-2,6-disubstituted-tetrahydropyrans. The reaction was found to proceed through a mixed silyl acetal intermediate.