Asymmetric catalytic n -phosphonyl imine chemistry: The use of primary free amino acids and Et 2AlCN for asymmetric catalytic strecker reaction

Parminder Kaur, Suresh Pindi, Walter Wever, Trideep Rajale, Guigen Li

Research output: Contribution to journalArticle

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Abstract

(Figure presented) 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 Et 2AlCN as nucleophile. This work also presents the novel use of nonvolatile and inexpensive Et 2AlCN in asymmetric catalysis. The N-phosphonyl protecting group enabled simple product purification to be achieved simply by washing the crude products with hexane, which is defined as the GAP chemistry (GAP: Group-Assistant-Purification).(17)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.

Original languageEnglish
Pages (from-to)5144-5150
Number of pages7
JournalJournal of Organic Chemistry
Volume75
Issue number15
DOIs
StatePublished - Aug 6 2010

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