1. The GAP chemistry for chiral N-phosphonyl imine-based Strecker reaction.
- Author
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Kaur, Parminder, Wever, Walter, Pindi, Suresh, Milles, Raizada, Gu, Peng, Shi, Min, and Li, Guigen
- Subjects
AMINO acid synthesis ,CHEMICAL reactions ,IMINES ,CHIRALITY ,ELECTROPHILES ,CYANIDES ,CHROMATOGRAPHIC analysis - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2011
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