1310539-57-1Relevant articles and documents
The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction
Kaur, Parminder,Wever, Walter,Pindi, Suresh,Milles, Raizada,Gu, Peng,Shi, Min,Li, Guigen
experimental part, p. 1288 - 1292 (2011/06/25)
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, α-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 α-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.