A mechanistic study of the Mitsunobu esterification reaction
β Scribed by Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J.
- Book ID
- 120162220
- Publisher
- American Chemical Society
- Year
- 1988
- Tongue
- English
- Weight
- 647 KB
- Volume
- 110
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
optically active (R)-cyanohydrins have been transformed into cyanohydrin esters of opposite configuration under Mitsunobu conditions and subsequently solvolyxed to (S)-cyanohydrins in high chemical and optical yield. The method works well for allylic sod benxylic cyaaohydrins. Cyanohytis containing
Resin-bound hydroxyl groups were esterified by N-protected amino acids using triphenylphosphine and diethyl azodicarboxylate (Mitsunobu reaction) in tetrahydrofuran or dimethylformamide. The typical reaction time was 1 h and the yield for different amino acids varied from 65 to 100%. No racemization