Catalytic enantioselective Michael addition in the synthesis of α-aminophosphonates |
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| Affiliation: | 1. Departamento de Química Orgánica I, Unidad Asociada al CSIC, Universidad Complutense de Madrid, Madrid, Spain;2. Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas, IQOG-CSIC, Madrid, Spain;1. Smithsonian Tropical Research Institute, Apartado 0843-03092, Balboa, Ancon, Panama;2. College of Marine and Environmental Sciences, James Cook University, Cairns, Queensland 4878, Australia;3. Faculty of Agriculture and Life Sciences, PO Box 85084, Lincoln University, Lincoln 7647, Christchurch, New Zealand;4. Institute of Biology, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark;5. CSIRO Agriculture, PO Box 1600, Canberra, Australian Capital Territory 2601, Australia |
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| Abstract: | Enantioenriched (S)-phosphoglutaminic acid derivatives with up to 72% ee were obtained in the catalytic enantioselective Michael reaction of the achiral phosphoglycine synthon. The scope and limitation of the process in terms of the catalyst (diverse (R,R)-TADDOL derivatives) and the base (solid alkali metal tert-butoxides) were examined. The nature of the transition complex was also investigated. |
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