ethyl (2R,3S)-3-formyl-2-(4-methoxyphenylamino)butanoate | 1010694-02-6

• 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: ethyl (2R,3S)-3-formyl-2-(4-methoxyphenylamino)butanoate
• 英文别名: ethyl (2R,3S)-2-(4-methoxyanilino)-3-methyl-4-oxobutanoate
• CAS: 1010694-02-6
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: UHCCICKUDVLYGF-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)- 、 丙醛 在 (R)-吡咯烷-3-羧酸 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 ethyl (2R,3S)-3-formyl-2-(4-methoxyphenylamino)butanoate 、 ethyl 2-(4-Methoxyphenylamino)-3-methyl-4-oxobutanoate
  参考文献：
  名称：

  Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions:  Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol

  摘要：

  The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with a-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the beta-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.

  DOI：

  10.1021/ja074907+

文献信息

• Direct catalytic asymmetric anti-selective Mannich-type reactions
  作者：Ismail Ibrahem、Armando Córdova

  DOI：10.1039/b602221a

  日期：——

  The simple chiral pyrrolidine catalyzed asymmetric anti-selective Mannich-type reaction is presented; the reaction gives the corresponding amino acid derivatives with 10:1- >19:1 dr and 97-99% ee.

  提出了简单的手性吡咯烷催化的不对称抗选择性曼尼希型反应。反应得到相应的氨基酸衍生物，其dr为10：1-> 19：1，ee为97-99％。
• Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective <i>anti</i>-Mannich-Type Reactions:  Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol
  作者：Haile Zhang、Susumu Mitsumori、Naoto Utsumi、Masanori Imai、Noemi Garcia-Delgado、Maria Mifsud、Klaus Albertshofer、Paul Ha-Yeon Cheong、K. N. Houk、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1021/ja074907+

  日期：2008.1.1

  The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with a-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the beta-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.