A formal [3+3] cycloaddition reaction. 5. An enantioselective intramolecular formal aza-[3+3] cycloaddition reaction promoted by chiral amine salts
A formal [3+3] cycloaddition reaction. 5. An enantioselective intramolecular formal aza-[3+3] cycloaddition reaction promoted by chiral amine salts
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DOI：
10.1021/jo050171s
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发表时间：
2005-05-27
影响因子：
3.6
通讯作者：
Slafer, B
中科院分区：
文献类型：
--
作者：
Gerasyuto, AI;Hsung, RP;Slafer, B
本文首次详细介绍了手性仲胺盐促进的分子内不对称选择性的氮杂[3 + 3]环加成反应。研究了手性胺的结构特征对对映选择性的影响。这项研究还揭示了一个非常有趣的逆转的立体化学在各自的环加合物使用C-1-和C-2-对称胺盐。此外，溶剂，抗衡阴离子，和温度的对映选择性的影响进行了描述，并提出了一个统一的机理模型的基础上，实验结果以及半经验计算。
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.