Two-step Synthesis and Synthetic Applications of Optically Active 4-Hydroxymethyl-4-phenyl-2-oxazolidinones

DOI

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Other Title
  • 光学活性4-ヒドロキシメチル-4-フェニル-2-オキサゾリジノン体の２段階合成とその応用

Description

Optically active (4S,αR)- and (4R,αR)-4-hydroxymethyl-4-phenyl-3-(α-methylbenzyl)-2-oxazolidinones (7a and 7b, respectively) were synthesized via a two-step synthesis. The first reaction was Petasis reaction using dihydroxyacetone, (R)-α-methylbenzylamine, and phenylboronic acid to afford (R)-2-(α-methylbenzyl)amino-2-phenyl-1,3-propanediol (4), and the second reaction was asymmetric desymmetrization of 4 using 2-chloroethyl chloroformate, Et3N, DMAP in CH2Cl2 and then DBU gave 7a and 7b in 49 and 24 % yields, respectively. Synthetic application of 7a was also investigated. After removal of the α-methylbenzyl group of 7a by TfOH and anisole in MeCN in 50 °C, hydroxylmethyl group of the product was converted smoothly into other functional groups. Thus, 7a would be a useful synthetic intermediate for optically active compounds possessing quaternary asymmetric centers.

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Details 詳細情報について

  • CRID
    1390282680611307904
  • NII Article ID
    130006997003
  • DOI
    10.14895/hannou.31.0.124.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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