Diastereoselective Formation of (Z)-Didehydroamino Acid Esters
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (05) , 487-490
- https://doi.org/10.1055/s-1992-26143
Abstract
The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.Keywords
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