The mechanism of the Mitsunobu esterification reaction. Part II. The involvement of (acyloxy)alkoxyphosphoranes
β Scribed by Camp, David; Jenkins, Ian D.
- Book ID
- 120464104
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 831 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
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
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