The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction

Parminder Kaur, Walter Wever, Suresh Pindi, Raizada Milles, Peng Gu, Min Shi, Guigen Li

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Abstract

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.

Original languageEnglish
Pages (from-to)1288-1292
Number of pages5
JournalGreen Chemistry
Volume13
Issue number5
DOIs
StatePublished - May 4 2011

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    Kaur, P., Wever, W., Pindi, S., Milles, R., Gu, P., Shi, M., & Li, G. (2011). The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction. Green Chemistry, 13(5), 1288-1292. https://doi.org/10.1039/c1gc15029d