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A mechanistic study of the Mitsunobu esterification reaction

✍ 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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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

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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