(4S)-4-tert-butyl-2-((E)-2-phenylethenyl)-2-oxazoline | 137542-79-1

• 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: (4S)-4-tert-butyl-2-((E)-2-phenylethenyl)-2-oxazoline
• 英文别名: (4S)-4-tert-butyl-2-[(E)-2-phenylethenyl]-4,5-dihydro-1,3-oxazole
• CAS: 137542-79-1
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: CLHWKUCLBIDZTD-WTNCMQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-4-tert-butyl-2-((E)-2-phenylethenyl)-2-oxazoline 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 生成 (S)-4,4-dimethyl-3-phenylpentan-1-ol
  参考文献：
  名称：

  Asymmetric Michael additions to .alpha.,.beta.-unsaturated oxazolines. An efficient preparation of chiral .beta.,.beta.-disubstituted propionaldehydes

  摘要：

  A short stereoselective route to a variety of chiral, nonracemic alpha,beta-unsaturated oxazolines derived from (S)-tert-leucinol is described. Addition of organolithium reagents to this chiral oxazoline occurs in a Michael fashion, giving rise to adducts with high diastereoselectivity. Reductive cleavage of the oxazoline leaves the beta,beta-disubstituted aldehydes in > 93% ee. This process represents a significant improvement in one of the earliest asymmetric conjugate additions first reported in 1975.

  DOI：

  10.1021/jo00025a027
• 作为产物：
  描述：

  (S)-4-tert-butyl-2-methyl-Δ²-oxazoline 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 (4S)-4-tert-butyl-2-((E)-2-phenylethenyl)-2-oxazoline
  参考文献：
  名称：

  Asymmetric Michael additions to .alpha.,.beta.-unsaturated oxazolines. An efficient preparation of chiral .beta.,.beta.-disubstituted propionaldehydes

  摘要：

  A short stereoselective route to a variety of chiral, nonracemic alpha,beta-unsaturated oxazolines derived from (S)-tert-leucinol is described. Addition of organolithium reagents to this chiral oxazoline occurs in a Michael fashion, giving rise to adducts with high diastereoselectivity. Reductive cleavage of the oxazoline leaves the beta,beta-disubstituted aldehydes in > 93% ee. This process represents a significant improvement in one of the earliest asymmetric conjugate additions first reported in 1975.

  DOI：

  10.1021/jo00025a027

文献信息

• Asymmetric conjugate additions to chiral α,β-unsaturated oxazolines with sulfonyl carbanions
  作者：Laura F Basil、A.I Meyers、A Hassner

  DOI：10.1016/s0040-4020(01)01151-6

  日期：2002.1

  Addition of sulfonyl carbanions with or without an electrophilic tether has been shown, under certain conditions, to add to alpha,beta-unsaturated oxazolines in good yields and high de's. When 4-bromobutylsulfonyl carbanions are added to unsaturated oxazolines, three contiguous stereocenters are formed and good yields of 1,2,3-substituted cyclohexanes are obtained as a 5:1 mixture of only two diastereomers. The sulfonyl substituent may be reductively cleaved to form selectively 1,2-disubstituted cyclohexanes. (C) 2002 Published by Elsevier Science Ltd.
• Asymmetric Michael additions to .alpha.,.beta.-unsaturated oxazolines. An efficient preparation of chiral .beta.,.beta.-disubstituted propionaldehydes
  作者：A. I. Meyers、Michael Shipman

  DOI：10.1021/jo00025a027

  日期：1991.12

  A short stereoselective route to a variety of chiral, nonracemic alpha,beta-unsaturated oxazolines derived from (S)-tert-leucinol is described. Addition of organolithium reagents to this chiral oxazoline occurs in a Michael fashion, giving rise to adducts with high diastereoselectivity. Reductive cleavage of the oxazoline leaves the beta,beta-disubstituted aldehydes in > 93% ee. This process represents a significant improvement in one of the earliest asymmetric conjugate additions first reported in 1975.