ethyl (R)-4-tert-butyl-2-oxazoline-2-carboxylate | 405940-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: ethyl (R)-4-tert-butyl-2-oxazoline-2-carboxylate
• 英文别名: ethyl (4S)-4-(1,1-dimethylethyl)-4,5-dihydrooxazole-2-carboxylate；ethyl (4S)-4-tert-butyl-4,5-dihydro-1,3-oxazole-2-carboxylate
• CAS: 405940-78-5
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: VTBYTEHRPKKEKX-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methoxyphenylmagnesium bromide 、 ethyl (R)-4-tert-butyl-2-oxazoline-2-carboxylate 以 四氢呋喃 为溶剂， 反应 16.0h， 以64%的产率得到(S)-2-[di(2'-methoxyphenyl)hydroxy]methyl-4-tert-butyl-2-oxazoline
  参考文献：
  名称：

  Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes

  摘要：

  Starting either from benzoylformic acid or ethyl oxamate and enantiopure beta-amino alcohols, several chiral alpha-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.038
• 作为产物：
  描述：

  L-叔亮氨醇 、 草酸酰胺乙酯 在 triethyloxonium fluoroborate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以43%的产率得到ethyl (R)-4-tert-butyl-2-oxazoline-2-carboxylate
  参考文献：
  名称：

  Highly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes

  摘要：

  A series of chiral C-2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11 : 1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branclied/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.

  DOI：

  10.1002/1522-2675(20011017)84:10<3178::aid-hlca3178>3.0.co;2-q

文献信息

• Highly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes
  作者：Frank Glorius、Markus Neuburger、Andreas Pfaltz

  DOI：10.1002/1522-2675(20011017)84:10<3178::aid-hlca3178>3.0.co;2-q

  日期：2001.10.17

  A series of chiral C-2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11 : 1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branclied/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.
• Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes
  作者：Carsten Bolm、Frank Schmidt、Lorenzo Zani

  DOI：10.1016/j.tetasy.2005.01.038

  日期：2005.4

  Starting either from benzoylformic acid or ethyl oxamate and enantiopure beta-amino alcohols, several chiral alpha-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. (c) 2005 Elsevier Ltd. All rights reserved.