The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction
The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction
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DOI：
10.1039/c1gc15029d
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发表时间：
2011-01-01
期刊：
影响因子：
9.8
通讯作者：
Li, Guigen
中科院分区：
文献类型：
--
作者：
Kaur, Parminder;Wever, Walter;Li, Guigen
手性N-膦酰亚胺被发现是有效的亲电试剂与二乙基氰化铝，一种非挥发性和廉价的氰化物源的反应。该反应以优异的化学产率（94-98%）和非对映选择性（95：5至> 99%）产生手性Strecker加合物α-氨基腈。证实该合成遵循差距化学（基团辅助纯化化学）过程，其可以避免传统的色谱和重结晶纯化，即，通过用己烷洗涤固体粗产物，可以简单地获得带有手性N-膦酰基的纯手性α-氨基腈。在弱酸性条件下，手性膦酰基助剂可以很容易地裂解，并通过正丁醇一次性萃取定量回收。
Chiral N-phosphonyl imines were found to be efficient electrophiles for reaction with diethylaluminium cyanide, a non-volatile and inexpensive cyanide source. The reaction produced chiral Strecker adducts, alpha-aminonitriles, in excellent chemical yields (94-98%) and diastereoselectivities (95 : 5 to > 99%). This synthesis was confirmed to follow the GAP chemistry (group-assistant-purification chemistry) process, which can avoid traditional chromatography and recrystallization purifications, i.e., the pure chiral alpha-aminonitriles bearing a chiral N-phosphonyl group can be simply obtained by washing the solid crude products with hexane. The chiral N-phosphonyl auxiliary can be easily cleaved under mildly acidic conditions and quantitatively recycled by a one-time extraction with n-butanol.