(2S,3S)-2,3-bis(phenylmethoxymethyl)aziridine | 134964-68-4

• 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: (2S,3S)-2,3-bis(phenylmethoxymethyl)aziridine
• CAS: 134964-68-4
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: KMKFIAAMPAVVEY-QZTJIDSGSA-N

物化性质

• 沸点：
  394.9±17.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-bis(phenylmethoxymethyl)aziridine 在 4-二甲氨基吡啶 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-1-((2S,3S)-2,3-Bis-benzyloxymethyl-aziridin-1-yl)-2-methyl-pent-4-en-1-one
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0
• 作为产物：
  描述：

  (S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane 在 lithium aluminium tetrahydride 、 sodium azide 、 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 丙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 (2S,3S)-2,3-bis(phenylmethoxymethyl)aziridine
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0

文献信息

• Aziridino alcohols as catalysts for the enantioselective addition of diethylzinc to aldehydes
  作者：David Tanner、Hanne T. Kornø、David Guijarro、Pher G. Andersson

  DOI：10.1016/s0040-4020(98)00875-8

  日期：1998.11

  The chiral aziridino alcohols 1 – 3 have been prepared either from amino acids (1a from serine; 1b – 1i and 3 from threonine; 2a – 2e from allo-threonine) or via asymmetric synthesis (1j, 1k, 1l and 2f from methyl cinnamate). These easily available ligands act as catalysts for the enantioselective addition of diethylzinc to benzaldehyde, with up to 90% stereoselectivity. The absolute configuration

  手性氮丙啶基醇1 - 3已经从氨基酸制备或者（1A从丝氨酸; 1B - 1I和3从苏氨酸;图2a -图2e从同种异体-苏氨酸），或通过不对称合成（1J，1K，1L和2F从肉桂酸甲酯）。这些容易获得的配体充当二乙基锌向苯甲醛对映选择性加成的催化剂，立体选择性高达90％。醇产物的绝对构型取决于氮丙啶环的取代模式，并提出了不同的过渡态模型来解释所观察到的对映选择性的转换。C 2酒石酸制备了对称的叠氮基叠氮二醇4a – 4h，并且还以较高的化学产率催化有机锌加成反应，并且高达94％的具有醚侧链的ee C 2对称配体5a – 5c效率较低（最高为46％ee）。除醛9-11外，还测试了最有效的配体（4c），ee最高为97％。
• C2-symmetric aziridines as efficient chiral auxiliaries
  作者：David Tanner、Carin Birgersson

  DOI：10.1016/s0040-4039(00)74374-7

  日期：1991.11

  The C2-symmetric aziridines 1 and 1' (available from (+)- and (-)-tartaric acid, respectively) are excellent chiral auxiliaries for asymmetric alkylation and aldol reactions.
• Hoshino, Jun'ichi; Hiraoka, Junko; Hata, Yasuo, Journal of the Chemical Society. Perkin transactions I, 1995, # 6, p. 693 - 698
  作者：Hoshino, Jun'ichi、Hiraoka, Junko、Hata, Yasuo、Sawada, Seiji、Yamamoto, Yukio

  DOI：——

  日期：——
• Tanner David, Birgersson Carin, Gogoll Adolf, Luthman Kristina, Tetrahedron, 50 (1994) N 32, S 9797-9824
  作者：Tanner David, Birgersson Carin, Gogoll Adolf, Luthman Kristina

  DOI：——

  日期：——