3-{2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyloxy]-ethylamino}-5,5-dimethyl-cyclohex-2-enone | 856015-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-{2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyloxy]-ethylamino}-5,5-dimethyl-cyclohex-2-enone
• CAS: 856015-63-9
• 化学式: C₂₀H₃₇NO₃Si
• 分子量: 367.604
• InChiKey: RPAMWNYLYZJKQA-HJWRWDBZSA-N

反应信息

• 作为反应物：
  描述：

  3-{2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyloxy]-ethylamino}-5,5-dimethyl-cyclohex-2-enone 在 manganese(IV) oxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 (Z)-4-[2-(5,5-Dimethyl-3-oxo-cyclohex-1-enylamino)-ethoxy]-but-2-enal
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s
• 作为产物：
  描述：

  (Z)-4-bromo-1-(tert-butyldimethylsilyloxy)but-2-ene 、 3-(2-hydroxyethylamino)-5,5-dimethylcyclohex-2-enone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以42%的产率得到3-{2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyloxy]-ethylamino}-5,5-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s