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 language | English |
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Pages (from-to) | 5144-5150 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 75 |
Issue number | 15 |
DOIs | |
State | Published - Aug 6 2010 |