Asymmetric synthesis of the 4-hydroxymethyl-2-oxazolidinone from the serinol derivative and chloroformates

✍ Scribed by Shigeo Sugiyama; Shoko Watanabe; Keitaro Ishii

• Book ID: 104262329
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 230 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01548-8

✦ Synopsis

Asymmetric desymmetrization of 2-[(etR)-et-methylbenzyl]amino-1,3-propanediol (1) with 2-chloroethyl chloroformate and DBU at room temperature gave optically active (4S)-4-hydroxymethyl-N-[(otR)-ot-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-[(otR)-~-methylbenzyl]aminopropyl carbonates [(2S)-4 and (2R)-4].