ChemInform Abstract: Inversion of the Configuration of Cyanohydrins by a Mitsunobu Esterification Reaction

Autor:	E. G. J. C. Warmerdam, A. Van Der Gen, C. G. Kruse, Johannes Brussee
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Allylic rearrangement Chemistry Yield (chemistry) Organic chemistry Mitsunobu reaction General Medicine Esterification reaction Optically active Racemization Cyanohydrin
Zdroj:	ChemInform. 24
ISSN:	0931-7597
Popis:	Optically active (R)-cyanohydrins have been transformed into cyanohydrin esters of opposite configuration under Mitsunobu conditions and subsequently solvolyzed to (S)-cyanohydrins in high chemical and optical yield. The method works well for allylic and benzylic cyanohydrins. Cyanohydrins containing strongly electron donating substituents gave extensive racemization. Saturated aliphatic cyanohydrins afforded esters in which the original configuration is retained. These results are discussed in terms of the mechanism of the Mitsunobu reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::045a8b6328b9a395b08e9898b3c55058 https://doi.org/10.1002/chin.199323050 Zobrazit plný text záznamu Plný text