Fine-tuned aminal cleavage:: A concise route to differentially protected enantiopure syn-α,β-diamino esters
Fine-tuned aminal cleavage:: A concise route to differentially protected enantiopure syn-α,β-diamino esters
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DOI：
10.1021/jo035613j
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发表时间：
2004-03-05
影响因子：
3.6
通讯作者：
Alonso, M
中科院分区：
文献类型：
--
作者：
Viso, A;de la Pradilla, RF;Alonso, M
对n -亚砜酰咪唑烷的动物裂解途径进行了研究，发现了在保持亚砜胺基不变的情况下，动物裂解部分的选择性条件。因此，在四氢呋喃中，用H3PO4水溶液处理对映纯n -亚砜基咪唑烷类化合物，可以得到产率很高的对映纯n -亚砜基二氨基酯，而甲醇作为助溶剂的存在，可以同时去除亚砜胺基团和动物裂解。这些底物在各种化学转化中的行为已经被探索。
A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.