di-tert-butyl (2R,2'R)-[2,2'-biindoline]-1,1'-dicarboxylate | 1239600-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: di-tert-butyl (2R,2'R)-[2,2'-biindoline]-1,1'-dicarboxylate
• 英文别名: (2R,2'R)-N,N'-bis(tert-butoxycarbonyl)biindoline；tert-butyl (2R)-2-[(2R)-1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydroindol-2-yl]-2,3-dihydroindole-1-carboxylate
• CAS: 1239600-48-6
• 化学式: C₂₆H₃₂N₂O₄
• 分子量: 436.551
• InChiKey: WKNMYNQDHDJIIX-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (2R,2'R)-[2,2'-biindoline]-1,1'-dicarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(2R,2'R)-2,2'-biindoline
  参考文献：
  名称：

  The attempted stereoselective synthesis of chiral 2,2′-biindoline

  摘要：

  The attempted first stereoselective synthesis of 2,2'-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the heteroatom protecting groups in key intermediates did not enhance the outcome of the Sharpless AD reaction. Therefore a limitation of this AD reaction is the use of 1,4-substituted but-2-enes where these substituents are ortho-substituted aromatics. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.035
• 作为产物：
  描述：

  1-Boc-吲哚啉 在 仲丁基锂 、 鹰爪豆碱 、 3C₆H₁₄S*CuI 、 iso-propyl 2,4-dinitrobenzoate 作用下， 以 乙醚 、 环己烷 、 四氢呋喃 为溶剂， 反应 7.0h， 以68%的产率得到di-tert-butyl (2R,2'R)-[2,2'-biindoline]-1,1'-dicarboxylate
  参考文献：
  名称：

  Method for Highly Enantioselective Ligation of Two Chiral C(sp³) Stereocenters

  摘要：

  A method is described for the joining of two alpha-lithiated C(sp(3)) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R2CuLi, by i-propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at -90 degrees C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.

  DOI：

  10.1021/jacs.7b07366

文献信息

• Method for Highly Enantioselective Ligation of Two Chiral C(sp³) Stereocenters
  作者：Eswar Bhimireddy、E. J. Corey

  DOI：10.1021/jacs.7b07366

  日期：2017.8.16

  A method is described for the joining of two alpha-lithiated C(sp(3)) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R2CuLi, by i-propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at -90 degrees C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.
• The attempted stereoselective synthesis of chiral 2,2′-biindoline
  作者：Mary J. Gresser、Steven M. Wales、Paul A. Keller

  DOI：10.1016/j.tet.2010.06.035

  日期：2010.8

  The attempted first stereoselective synthesis of 2,2'-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the heteroatom protecting groups in key intermediates did not enhance the outcome of the Sharpless AD reaction. Therefore a limitation of this AD reaction is the use of 1,4-substituted but-2-enes where these substituents are ortho-substituted aromatics. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.