(R)-3-(2-(naphthalen-2-yl)pent-4-enoyl)oxazolidin-2-one | 1181399-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3-(2-(naphthalen-2-yl)pent-4-enoyl)oxazolidin-2-one
• CAS: 1181399-03-0
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: BITJLVCUNRPNQE-MRXNPFEDSA-N

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 3-(2-(naphthalen-2-yl)acetyl)oxazolidin-2-one 在 caesium hydroxide monohydrate 、 2,7-bis[O(9)-allylhydrocinchonidinium-N-methyl]naphthalene dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 3-(2-(naphthalen-2-yl)pent-4-enoyl)oxazolidin-2-one 、 (R)-3-(2-(naphthalen-2-yl)pent-4-enoyl)oxazolidin-2-one
  参考文献：
  名称：

  Phase-transfer catalyzed asymmetric arylacetate alkylation

  摘要：

  Phenethyl arylacetates are alkylated under phase-transfer conditions with cinchona catalysts with alkyl halides in high yield with excellent enantioselectivity (84-99% ee) following recrystallization. Cinchonidine (CD) derived catalyst gave the (R)-product and cinchonine (CN) catalyst produced the (S)-product. The phenethyl (PE) ester group is removed, using ammonium formate and catalytic Pd/C, to give alkylated carboxylic acid products in high selectivity. The utility of the approach is demonstrated by a direct synthesis of (S)-naproxen(TM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.090