(4R)-2,2-dimethyl-4-phenyl-3-[(E)-3-phenylpropenoyl]oxazolidine | 159463-49-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4R)-2,2-dimethyl-4-phenyl-3-[(E)-3-phenylpropenoyl]oxazolidine
• 英文别名: (R)-3-Cinnamoyl-2,2-dimethyl-4-phenyloxazolidine；(E)-1-[(4R)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]-3-phenylprop-2-en-1-one
• CAS: 159463-49-7
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: DTXPJTHOTSQOQX-JKGDOXCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-2,2-dimethyl-4-phenyl-3-[(E)-3-phenylpropenoyl]oxazolidine 以91%的产率得到
  参考文献：
  名称：

  Kanemasa Shuji, Suenaga Hiroyuki, Onimura Kenjiro, J. Org. Chem, 59 (1994) N 23, S 6949-6954

  摘要：

  DOI：
• 作为产物：
  描述：

  D-苯甘氨醇 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 (4R)-2,2-dimethyl-4-phenyl-3-[(E)-3-phenylpropenoyl]oxazolidine
  参考文献：
  名称：

  Effective Enantiocontrol in Conjugate Additions of Organocuprates. Highly Selective 1,5-Chiral Induction in the Conjugate Additions of Cuprates to .alpha.,.beta.-Unsaturated Amide Derivatives of 2,2-Dimethyloxazolidine Chiral Auxiliaries

  摘要：

  alpha,beta-Unsaturated amide derivatives of 2,2-dimethyloxazolidines, developed as new chirality-controlling auxiliaries based on the restricted rotation of the amide linkage, have been applied to the enantiocontrol of conjugate additions of lithium and magnesium cuprates. High selectivities of 1,5-chiral inductions are attained, indicating their promising synthetic potential in asymmetric synthesis. The diastereofacial selectivities depend upon the efficiency of steric shielding by the 4-substituent of the chiral auxiliary, and the reaction of (S)-4-benzyl-3-[(E)-2-butenoyl]-2,2,5,5-tetramethyloxazolidine with Ph(2)CuMgBr.MgBrI is exclusively lk-1,5-inductive. Use of organolithium and organomagnesium show opposite low selectivities. It is concluded that the stereochemistry of cuprate conjugate addition is determined at the step of formation of the d,pi* type charge transfer complexes.

  DOI：

  10.1021/jo00102a018

文献信息

• Racemic and asymmetric cobalt-catalysed reductive aldol couplings of α,β-unsaturated amides with ketones
  作者：Ralph J.R. Lumby、Pekka M. Joensuu、Hon Wai Lam

  DOI：10.1016/j.tet.2008.06.022

  日期：2008.8

  In the presence of diethylzinc as a stoichiometric reductant, substoichiometric quantities of an appropriate cobalt source catalyse diastereoselective reductive aldol coupling reactions of α,β-unsaturated amides with ketones. The use of a readily available oxazolidine as a chiral auxiliary imparts high levels of asymmetric induction in these reactions.

  在二乙基锌作为化学计量的还原剂的存在下，亚化学计量的适当的钴源催化α，β-不饱和酰胺与酮的非对映选择性还原羟醛偶联反应。在这些反应中，容易获得的恶唑烷用作手性助剂会引起高水平的不对称诱导。
• Enantiopure epoxidation of electrophilic alkenes
  作者：Otto Meth-Cohn、Yi Chen、David J. Williams

  DOI：10.1039/b000520g

  日期：——

  Cinnamamides derived from prolinols (e.g. –CH2OH and –CPh2OH) and from proline amides (e.g. prolineanilide) are epoxidised with total retention of the alkene configuration, to give either epoxides or bicyclic derivatives thereof, essentially enantiopure, using tert-butyl hydroperoxide and butyllithium.

  由脯氨醇（如-CH2OH和-CPh2OH）和脯氨酸酰胺（如脯氨酸苯胺）衍生的肉桂酰胺，在使用叔丁基过氧化氢和丁基锂进行环氧化时，可完全保留烯构型，得到环氧化物或其双环衍生物，基本上是不纯的。
• Kanemasa Shuji, Suenaga Hiroyuki, Onimura Kenjiro, J. Org. Chem, 59 (1994) N 23, S 6949-6954
  作者：Kanemasa Shuji, Suenaga Hiroyuki, Onimura Kenjiro

  DOI：——

  日期：——
• Effective Enantiocontrol in Conjugate Additions of Organocuprates. Highly Selective 1,5-Chiral Induction in the Conjugate Additions of Cuprates to .alpha.,.beta.-Unsaturated Amide Derivatives of 2,2-Dimethyloxazolidine Chiral Auxiliaries
  作者：Shuji Kanemasa、Hiroyuki Suenaga、Kenjiro Onimura

  DOI：10.1021/jo00102a018

  日期：1994.11

  alpha,beta-Unsaturated amide derivatives of 2,2-dimethyloxazolidines, developed as new chirality-controlling auxiliaries based on the restricted rotation of the amide linkage, have been applied to the enantiocontrol of conjugate additions of lithium and magnesium cuprates. High selectivities of 1,5-chiral inductions are attained, indicating their promising synthetic potential in asymmetric synthesis. The diastereofacial selectivities depend upon the efficiency of steric shielding by the 4-substituent of the chiral auxiliary, and the reaction of (S)-4-benzyl-3-[(E)-2-butenoyl]-2,2,5,5-tetramethyloxazolidine with Ph(2)CuMgBr.MgBrI is exclusively lk-1,5-inductive. Use of organolithium and organomagnesium show opposite low selectivities. It is concluded that the stereochemistry of cuprate conjugate addition is determined at the step of formation of the d,pi* type charge transfer complexes.