(S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate | 197460-37-0

• 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)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[hydroxy(diphenyl)methyl]-2,3-dihydroindole-1-carboxylate
• CAS: 197460-37-0
• 化学式: C₂₆H₂₇NO₃
• 分子量: 401.505
• InChiKey: GLXWHBZSKZDYIS-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate 在 四甲基乙二胺 、 六氯乙烷 、 仲丁基锂 作用下， 生成 tert-butyl (2S)-7-chloro-2-[hydroxy(diphenyl)methyl]-2,3-dihydroindole-1-carboxylate
  参考文献：
  名称：

  Asymmetric Deprotonations:  Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/(−)-Sparteine

  摘要：

  The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.

  DOI：

  10.1021/jo9708856
• 作为产物：
  描述：

  (S)-7-Chloro-2-trimethylstannanyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 在 正丁基锂 、 仲丁基锂 、 鹰爪豆碱 作用下， 反应 7.0h， 生成 (S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate
  参考文献：
  名称：

  Asymmetric Deprotonations:  Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/(−)-Sparteine

  摘要：

  The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.

  DOI：

  10.1021/jo9708856

文献信息

• Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines
  作者：Truong-Giang Le、Hoai-Thu Pham、James P. Martin、Isabelle Chataigner、Jean-Luc Renaud

  DOI：10.1080/00397911.2020.1778034

  日期：2020.9.1

  first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100)

  摘要在此，我们介绍了 1,2-二氢吡啶不对称有机催化合成的第一个例子，提供了对映选择性访问并部分解决了二氢吡啶合成中的区域选择性挑战。我们证明，通过有机催化剂的改性，可以以高区域选择性（1,2-DHP/1,4-DHP 的比率）获得 1,2- 和 1,4- 二氢吡啶（1,2- 和 1,4-DHP）从 95/5 到 0/100）和对映选择性（1,2-DHP 的 ee 为 33%，1,4-DHP 的 ee 高达 98%），产率高（高达 87%）。图形概要
• Enantioselective Reformatsky Reaction of Ketones Catalyzed by Chiral Indolinylmethanol
  作者：Renshi Luo、Miao-Miao Chen、Lu Ouyang、Albert S. C. Chan、Gui Lu

  DOI：10.1002/ejoc.202000768

  日期：2020.8.16

  Asymmetric Reformatsky reaction of ethyl iodide acetate with ketones was realized via the initiation of Me2Zn and the proper stereocontrol of the chiral Zn‐indolinylmethanol complex. Various chiral β‐hydroxyl carbonyl compounds were obtained in good yields and excellent enantioselectivities (up to 97 % ee ).

  通过引发Me 2 Zn和适当控制手性Zn-吲哚基甲醇络合物的立体控制，实现了乙酸乙酯与酮的不对称Reformatsky反应。以高收率和出色的对映选择性（高达97％ee）获得了各种手性β-羟基羰基化合物。
• Asymmetric Deprotonations:  Lithiation of <i>N</i>-(<i>tert</i>-Butoxycarbonyl)indoline with <i>sec</i>-Butyllithium/(−)-Sparteine
  作者：Kathleen M. Bertini Gross、Young M. Jun、Peter Beak

  DOI：10.1021/jo9708856

  日期：1997.10.1

  The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.