Asymmetric three-component Strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N'-dioxides.
Asymmetric three-component Strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N'-dioxides.
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DOI：
10.1002/chem.200800319
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发表时间：
2008-07
期刊：
影响因子：
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通讯作者：
Y. Wen;B. Gao;Yingzi Fu;S. Dong;Xiaohua Liu;Xiaoming Feng
中科院分区：
文献类型：
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作者：
Y. Wen;B. Gao;Yingzi Fu;S. Dong;Xiaohua Liu;Xiaoming Feng
新型反式-4-羟基-L-脯氨酸衍生的N，N '-二氧化物已被开发并用作醛、（1，1-二苯基）甲胺和TMSCN的一锅三组分Strecker反应的有效有机催化剂。芳香族和脂肪族醛被认为是合适的底物。在温和条件下，以高达95%ee（ee=对映体过量）的高产率获得相应的α-氨基腈。经一次重结晶可得到光学纯的产物。该催化剂可以由反式-4-羟基-L-脯氨酸和二胺经三步容易地制备。根据实验结果和所观察到的产物的绝对构型，提出了一个可能的过渡态来解释不对称诱导的起源。
Novel trans-4-hydroxy-L-proline-derived N,N'-dioxides have been developed and used as efficient organocatalysts for the one-pot three-component Strecker reaction with an aldehyde, (1,1-diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes were found to be suitable substrates. The corresponding alpha-amino nitriles were obtained in high yields with up to 95 % ee (ee=enantiomeric excess) under mild conditions. Optically pure products could be obtained after a single recrystallization. The catalyst can be easily prepared from trans-4-hydroxy-L-proline and a diamine in three steps. Based on the experimental results and the observed absolute configurations of the products, a possible transition state has been proposed to explain the origin of the asymmetric induction.