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Stereochemistry of the Tetrabutylammonium Cyanide‐Catalyzed Cyanosylilation of Cyclic α,β‐Epoxyketones – Dependence of the Diastereoselectivity on the Ring Size
Author(s) -
Aljarilla Ana,
Córdoba Rubén,
Csaky Aurelio G.,
Fernández Israel,
López Ortiz Fernando,
Plumet Joaquín,
Ruiz Gómez Gloria
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600239
Subject(s) - chemistry , ring (chemistry) , ring size , catalysis , cyanide , medicinal chemistry , stereochemistry , organic chemistry
The diastereoselective Bu 4 NCN‐catalyzed addition of TMSCN to cyclic α,β‐epoxyketones has been considered. Good diastereoselectivities were found, depending on the ring size of the starting material. Computational studies account for the observed diastereoselectivities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)