Asymmetric catalytic N-phosphonyl imine chemistry: the use of primary free amino acids and Et2AlCN for asymmetric catalytic Strecker reaction.
Asymmetric catalytic N-phosphonyl imine chemistry: the use of primary free amino acids and Et2AlCN for asymmetric catalytic Strecker reaction.
复制标题
DOI：
10.1021/jo100865q
复制
发表时间：
2010-08-06
影响因子：
3.6
通讯作者：
Li, Guigen
中科院分区：
文献类型：
--
作者：
Kaur, Parminder;Pindi, Suresh;Wever, Walter;Rajale, Trideep;Li, Guigen
建立了一种新的非手性膦酰亚胺的不对称催化Strecker反应。以游离氨基酸为催化剂，Et_2AlCN为亲核试剂，对映选择性（95.2-99.7%ee）和产率（89-97%）都很好。这项工作还提出了新的使用非挥发性和廉价的Et 2AlCN在不对称催化。N-膦酰基保护基使得能够简单地通过用己烷洗涤粗产物来实现简单的产物纯化。在温和的条件下，它也可以容易地裂解和循环，以定量回收N，N′-双（萘-1-基甲基）乙烷-1，2-二胺。提出了一种新的反应机理，并得到了实验观察的支持。
The new asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines has been established. Excellent enantioselectivity (95.2–99.7%ee) and yields (89–97%) have been achieved by using primary free natural amino acids as catalysts and Et2AlCN as nucleophile. This work also presents the novel use of non-volatile and inexpensive Et2AlCN in asymmetric catalysis. The N-phosphonyl protecting group enabled simple product purification to be achieved simply by washing the crude products with hexane. It can also be readily cleaved and recycled under mild condition to give a quantitative recovery of N,N′-bis(naphthalen-1-ylmethyl)ethane-1,2-diamine. A new mechanism was proposed for this reaction and was supported by experimental observations.
登录
查看更多内容
影响因子：
3
作者：
Ai, Teng;Han, Jianlin;Li, Guigen
通讯作者：
Li, Guigen
影响因子：
--
作者：
Nakamura, S;Sato, N;Toru, T
通讯作者：
Toru, T
影响因子：
1.8
作者：
Benedetti, F;Berti, F;Norbedo, S
通讯作者：
Norbedo, S
影响因子：
--
作者：
Gille, Segolene;Cabello, Noemi;Alexakis, Alexandre
通讯作者：
Alexakis, Alexandre
影响因子：
5.2
作者：
Li, GG;Wei, HX;Kim, SH
通讯作者：
Kim, SH