(1R,3R)-3-[(E)-2-tert-Butoxycarbonyl-2-(4-methoxy-benzenesulfonyl)-vinyl]-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester | 130051-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3R)-3-[(E)-2-tert-Butoxycarbonyl-2-(4-methoxy-benzenesulfonyl)-vinyl]-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester
• CAS: 130051-23-9
• 化学式: C₂₁H₂₈O₇S
• 分子量: 424.515
• InChiKey: PGQZETRITVTYMY-MREAOZFUSA-N

反应信息

• 作为反应物：
  描述：

  (1R,3R)-3-[(E)-2-tert-Butoxycarbonyl-2-(4-methoxy-benzenesulfonyl)-vinyl]-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester 在 sodium dithionite 、 甲基三辛基氯化铵 、 碳酸氢钠 作用下， 以 环己烷 、 水 为溶剂， 反应 1.0h， 以70%的产率得到(1R,3S)-3-((Z)-2-tert-Butoxycarbonyl-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034