(S)-4-benzyl-3-methoxyacetyl-2,2-dimethyloxazolidine

• 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: (S)-4-benzyl-3-methoxyacetyl-2,2-dimethyloxazolidine
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: PGOMUGPPEWKXQD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  巴豆酸甲酯 、 (S)-4-benzyl-3-methoxyacetyl-2,2-dimethyloxazolidine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以57%的产率得到(S)-4-benzyl-3-<2-methoxy-3-methyl-4-(methoxycarbonyl)butanoyl>-2,2-dimethyloxazolidine
  参考文献：
  名称：

  High enantiocontrol of michael additions by use of 2:2-dimethyloxazolidine chiral auxiliaries. Exclusively ul,lk-1,4-inductive michael additions of the lithium (z)-enolate of (s)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyl-oxazolidine to α,β-unsaturated esters

  摘要：

  The lithium (Z)-enolate generated from the propanamide of (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine undergoes highly lk-1,4/anti-selective Michael additions to alpha,beta-unsaturated ester and amide accepters. However, only poor selectivities result when either the lithium (Z)enolates of an oxazolidine methoxyacetamide derivative or the oxazolidine alpha,beta-unsaturated amide accepters are used. The observed high chiral inductions in the former cases are based on the facts that syn-conformation of the enolate is involved in the transition state where the enolate and oxazolidine planes are coplanar, and that the diastereoface remote from the 4-shielding substituent of the auxiliary is open for the attack of acceptor molecules.

  DOI：

  10.1016/0040-4020(95)00623-g
• 作为产物：
  描述：

  甲氧基乙酰氯 、 (4S)-2,2-dimethyl-4-phenylmethyloxazolidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(S)-4-benzyl-3-methoxyacetyl-2,2-dimethyloxazolidine
  参考文献：
  名称：

  High enantiocontrol of michael additions by use of 2:2-dimethyloxazolidine chiral auxiliaries. Exclusively ul,lk-1,4-inductive michael additions of the lithium (z)-enolate of (s)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyl-oxazolidine to α,β-unsaturated esters

  摘要：

  The lithium (Z)-enolate generated from the propanamide of (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine undergoes highly lk-1,4/anti-selective Michael additions to alpha,beta-unsaturated ester and amide accepters. However, only poor selectivities result when either the lithium (Z)enolates of an oxazolidine methoxyacetamide derivative or the oxazolidine alpha,beta-unsaturated amide accepters are used. The observed high chiral inductions in the former cases are based on the facts that syn-conformation of the enolate is involved in the transition state where the enolate and oxazolidine planes are coplanar, and that the diastereoface remote from the 4-shielding substituent of the auxiliary is open for the attack of acceptor molecules.

  DOI：

  10.1016/0040-4020(95)00623-g

文献信息

• High enantiocontrol of michael additions by use of 2:2-dimethyloxazolidine chiral auxiliaries. Exclusively ul,lk-1,4-inductive michael additions of the lithium (z)-enolate of (s)-4-benzyl-2,2,5,5-tetramethyl-3-propanoyl-oxazolidine to α,β-unsaturated esters
  作者：Shuji Kanemasa、Masafumi Nomura、Sachiyo Yoshinaga、Hidetoshi Yamamoto

  DOI：10.1016/0040-4020(95)00623-g

  日期：1995.9

  The lithium (Z)-enolate generated from the propanamide of (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine undergoes highly lk-1,4/anti-selective Michael additions to alpha,beta-unsaturated ester and amide accepters. However, only poor selectivities result when either the lithium (Z)enolates of an oxazolidine methoxyacetamide derivative or the oxazolidine alpha,beta-unsaturated amide accepters are used. The observed high chiral inductions in the former cases are based on the facts that syn-conformation of the enolate is involved in the transition state where the enolate and oxazolidine planes are coplanar, and that the diastereoface remote from the 4-shielding substituent of the auxiliary is open for the attack of acceptor molecules.