(1'R)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole | 173541-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (1'R)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole
• 英文别名: tert-butyl-dimethyl-[1-[(1R)-1-phenylethyl]pyrrol-2-yl]oxysilane
• CAS: 173541-18-9
• 化学式: C₁₈H₂₇NOSi
• 分子量: 301.504
• InChiKey: ZLJJOSLZCQUOON-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1'R)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole 在 palladium on activated charcoal sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 碘 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-2-Dimethoxymethyl-1-((R)-1-phenyl-ethyl)-pyrrolidine
  参考文献：
  名称：

  A new asymmetric approach towards 2-pyrrolidinones and pyrrolidines: Simple versus double stereodifferentiation

  摘要：

  The condensation of a chiral 2-silyloxypyrrole derivative with achiral and chiral formyl cation equivalents has been studied for the first time. The methodology allows to build-up pyroglutammic aldehydes and prolinal systems with a stereocontrol from good to excellent. Whereas the chiral auxiliary residing on the pyrrole system shows an intrinsic good level of diastereoface discrimination at C-5, the combined use of a 2-methoxy-3-tosyl-oxazolidine as a chiral formylating agent allows a total stereocontrol of the condensation. A rationale for the observed stereochemical outcome is presented.

  DOI：

  10.1016/0040-4039(95)01788-j
• 作为产物：
  描述：

  (1'R)-1-(1'-phenylethyl)-1H-pyrrole 在 双氧水 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 192.67h， 生成 (1'R)-1-(1'-phenylethyl)-2-tert-butyldimethylsilyloxy-1H-pyrrole
  参考文献：
  名称：

  A new asymmetric approach toward 5-substituted pyrrolidin-2-one derivatives

  摘要：

  The condensation between a chiral 2-silyloxypyrrole and either achiral or chiral formyl cation equivalents has been studied. The methodology has allowed to build-up 5-substituted pyrrolidin-2-one derivatives with a stereocontrol from good to excellent. The chiral auxiliary located on the silyloxypyrrole showed an intrinsic good level of diastereoface discrimination at C-5. However. the use of a 2-methoxy-3-tosyl-oxazolidine as chiral formylating agent allowed a total stereocontrol in the condensation. A rationale for the observed stereochemical outcome is presented. The stereoselective manipulation of these adducts provided new potentially interesting pyroglutamic aldehyde and prolinal derivatives. whereas treatment with TiCl4 triggered unexpectedly a Pomeranz-Fritsch type intramolecular condensation affording a benzocondensated indolizidinone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00494-3