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Asymmetric synthesis of cephems from chiral alpha thiocarbamylaminoesters



Asymmetric synthesis of cephems from chiral alpha thiocarbamylaminoesters



Bulletin de la Societe Chimique de France 128(5): 760-772



This work describes a stereospecific and multistep synthesis of 7-amino-7-methyl cephems from chiral .alpha.-thiocarbamoylaminoesters resolved by covalent diastereoisomers using (S)-(-)-ethyl lactate as a chiral auxiliary. The chimioselective reduction of the introcyclic imine double bond of chiral .alpha.-(thiazin-2-yl)amino-esters, which are key intermediates built by a [4+2] cycloaddition reaction, gave the second asymmetric centre with a high stereoselectivity. The stereochemistry of the asymmetric centres was studied during the reaction of lactamisation requiring two steps at the end of the synthesis.

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