(1S,3R)-2,2,-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-1-(2-oxopropyl)cyclopropane | 144686-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R)-2,2,-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-1-(2-oxopropyl)cyclopropane
• CAS: 144686-76-0
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: FOGUOAYZADAALY-WDEREUQCSA-N

反应信息

• 作为产物：
  描述：

  (1S,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-1-<(2RS)-2-hydroxypropyl>cyclopropane 在 chromium(VI) oxide 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以77%的产率得到(1S,3R)-2,2,-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-1-(2-oxopropyl)cyclopropane
  参考文献：
  名称：

  Baker's yeast-induced asymmetric reduction of the keto group activated by the cyclopropane unit.

  摘要：

  Certain cis-3-substituted 2,2-dimethyl-1-(2-oxopropyl)-cyclopropanes are effectively reduced by baker's yeast to give predominantly (s)-isomers of the corresponding 2-hydroxypropyl derivatives. Reduction of the 2-oxopropyl group proceeds more rapidly (ca. 3.5 times) and with higher stereoselectivity [(S):(R) = 98:2] when the group is attached to the (s)-carbon of the cyclopropane unit than of the keto group attached to the (R)-carbon [(S):(R) = (88):(12)]. Yeast reduction of the keto derivatives is effectively carried out when substituents at C-3 are as follows: CH2COOCH3, -CH2COCH3, -CN, -CH2CN, -CH2CH2OH, and the relative rates of reduction are 36:36:15:13:7. No reduction occurs when substituents at C-3 are propyl, 2-methyl-2-hydroxypropyl or 2-methyl-1,3-dioxolan-2-yl methyl groups.

  DOI：

  10.1016/s0957-4166(00)82103-5