(S)-2-((E)-2-Naphthalen-1-yl-vinyl)-1-((R)-1-phenyl-ethyl)-aziridine | 909408-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-((E)-2-Naphthalen-1-yl-vinyl)-1-((R)-1-phenyl-ethyl)-aziridine
• CAS: 909408-45-3
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: WIYCBBGAWKRWRC-XGASYVDGSA-N

反应信息

• 作为反应物：
  描述：

  (S)-2-((E)-2-Naphthalen-1-yl-vinyl)-1-((R)-1-phenyl-ethyl)-aziridine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 叠氮基三甲基硅烷 、 氢气 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 (R)-4-Naphthalen-1-yl-N¹-((R)-1-phenyl-ethyl)-butane-1,2-diamine
  参考文献：
  名称：

  An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(1′R)-methylbenzyl]aziridine-2-yl]methanol

  摘要：

  Enantiomerically pure terminal 1,2-diamines, which can serve as precursors for the synthesis of many biologically important compounds, were synthesized efficiently from a commercially available chiral [1-(1'R)-methylbenzyl]aziridine-2-yl]methanol. Various enantiomerically pure 2-vinylaziridines were prepared by Wittig reactions from aziridine-2-carboxaldehyde and the corresponding phosphonium salts. The C(2)-N bond of the vinyl substituted aziridine ring was regioselectively cleaved by azidotrimethylsilane (TMSN3). The azido group and the double bond were reduced successively to give the target compounds in high yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.024
• 作为产物：
  描述：

  (R)-1-((R)-1-phenylethyl)aziridine-2-carbaldehyde 、 alkaline earth salt of/the/ methylsulfuric acid 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(S)-2-((E)-2-Naphthalen-1-yl-vinyl)-1-((R)-1-phenyl-ethyl)-aziridine
  参考文献：
  名称：

  An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(1′R)-methylbenzyl]aziridine-2-yl]methanol

  摘要：

  Enantiomerically pure terminal 1,2-diamines, which can serve as precursors for the synthesis of many biologically important compounds, were synthesized efficiently from a commercially available chiral [1-(1'R)-methylbenzyl]aziridine-2-yl]methanol. Various enantiomerically pure 2-vinylaziridines were prepared by Wittig reactions from aziridine-2-carboxaldehyde and the corresponding phosphonium salts. The C(2)-N bond of the vinyl substituted aziridine ring was regioselectively cleaved by azidotrimethylsilane (TMSN3). The azido group and the double bond were reduced successively to give the target compounds in high yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.024