(αR,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimido-β-methylbutanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (αR,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimido-β-methylbutanoate
• 英文别名: [(3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl] (2R)-2-(1,3-dioxoisoindol-2-yl)-3-methylbutanoate
• 化学式: C₂₅H₂₆N₂O₅
• 分子量: 434.492
• InChiKey: ZAGSUNWQUPGJRI-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻苯二甲基撷氨酸 在 氯化亚砜 、 4 A molecular sieve 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 生成 (αR,3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-phthalimido-β-methylbutanoate
  参考文献：
  名称：

  (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids

  摘要：

  rac-alpha-Amino acids (rac-1a-d) were formally deracemized by a four-step reaction sequence: (a) protection of the amino function as the phthalimido derivative; (b) acyl chloride formation; (c) diastereoselective reaction with the chiral auxiliaries (R)- or (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, (R)- or (S)-3; and (d) acid hydrolysis to deprotect both the ester and phthalimido functions. Diastereoselectivities of the intermediate esters 4 were good (82-96% d.e.), except for the case of 4b, (41% d.e.), the precursor of valine. The main diastereoisomer of esters 4 was (alpha R,3S)- or (alpha S,3R)-, except for 4d: in this case, working at -78 degrees C, the (alpha R,3R)-diastereoisomer was the main product, which epimerizes easily at the ex-position when at room temperature. Acid hydrolysis of esters 4 directly gave the deprotected alpha-amino acids, with little or no epimerization at the alpha-position of the alpha-amino acid and complete recovery of the chiral auxiliary. Only (alpha R,3R)-4d on acid hydrolysis partially epimerized at the alpha-position. Moreover, some alpha-amino acids and their N,N-dibenzyl derivatives were obtained by dynamic kinetic resolution of diastereoisomeric mixtures of alpha-bromo esters 5 derived from the chiral auxiliaries (R)- or (S)-3 during reaction with dibenzylamine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00018-x

文献信息

• (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids
  作者：Pelayo Camps、Francesc Pérez、Núria Soldevilla、Miguel A Borrego

  DOI：10.1016/s0957-4166(99)00018-x

  日期：1999.2

  rac-alpha-Amino acids (rac-1a-d) were formally deracemized by a four-step reaction sequence: (a) protection of the amino function as the phthalimido derivative; (b) acyl chloride formation; (c) diastereoselective reaction with the chiral auxiliaries (R)- or (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, (R)- or (S)-3; and (d) acid hydrolysis to deprotect both the ester and phthalimido functions. Diastereoselectivities of the intermediate esters 4 were good (82-96% d.e.), except for the case of 4b, (41% d.e.), the precursor of valine. The main diastereoisomer of esters 4 was (alpha R,3S)- or (alpha S,3R)-, except for 4d: in this case, working at -78 degrees C, the (alpha R,3R)-diastereoisomer was the main product, which epimerizes easily at the ex-position when at room temperature. Acid hydrolysis of esters 4 directly gave the deprotected alpha-amino acids, with little or no epimerization at the alpha-position of the alpha-amino acid and complete recovery of the chiral auxiliary. Only (alpha R,3R)-4d on acid hydrolysis partially epimerized at the alpha-position. Moreover, some alpha-amino acids and their N,N-dibenzyl derivatives were obtained by dynamic kinetic resolution of diastereoisomeric mixtures of alpha-bromo esters 5 derived from the chiral auxiliaries (R)- or (S)-3 during reaction with dibenzylamine. (C) 1999 Elsevier Science Ltd. All rights reserved.