Chiral Catalyst Optimization Using Both Solid-Phase and Liquid-Phase Methods in Asymmetric Aza Diels−Alder Reactions
- 4 April 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (9) , 1225-1227
- https://doi.org/10.1021/ol005656b
Abstract
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.Keywords
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