Abstract
Asymmetric desymmetrization of 2-[(αR)-α-methylbenzyl]amino-1,3-propanediol (1) with 2-chloroethyl chloroformate and DBU at room temperature gave optically active (4S)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone [(4S)-2] (up to 94% de). This reaction involves kinetic resolution and [1,3]-alkoxyacyl migration of 2-chloroethyl (2S)- and 2-chloroethyl (2R)-3-hydroxy-2-[(αR)-α-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4].
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