Chiral catalyst optimization using both solid-phase and liquid-phase methods in asymmetric aza Diels-Alder reactions |
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Authors: | Kobayashi Kusakabe Ishitani |
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Institution: | Graduate School of Pharmaceutical Sciences, University of Tokyo, Japan. |
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Abstract: | formula: see text] In the presence of 1-5 mol % of a chiral zirconium catalyst, aza Diels-Alder reactions of aldimines with Danishefsky's dienes proceeded smoothly to afford the corresponding piperidine derivatives in high yields with high enantioselectivities. For the catalyst optimization, solid-phase and liquid-phase methods were successfully used. In the solid-phase approach, polymer-supported (R)-1,1'-binaphthols (BINOLs) have been synthesized and rapid optimization using the solid-phase reactions has been achieved. On the other hand, novel chiral zirconium cyanides were developed as excellent catalysts using the liquid-phase approach. |
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