|
|||||
|
|
Anion reaction of 1,3-benzoxathiole-3-oxide with several electrophilic compounds |
|
| Authors: | Salvatore Cabiddu Enzo Cadoni Stefana Melis Gioanna Gelli Maria Grazia Cabiddu Claudia Fattuoni Stefania De Montis Sandra Ianelli |
| Institution: | a Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554 Bivio per Sestu, I-09042 Monserrato, Italy b Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica e Chimica Fisica, Università di Parma, Parco Area delle Scienze 17 A I-43100 Parma, Italy |
| Abstract: | The reaction of benzoxathiole-3-oxide with LDA in THF or THF/hexane or THF/HMPA gave a carbanion which was reacted with methyl iodide, aromatic aldehydes or carbon dioxide. The conformational stability ( -diastereoselectivity) of the carbanion and the asymmetric induction due to the prochiral electrophiles (β-diastereoselectivity) was studied. The temperature and the solvent effects on the - and β-diastereoselectivity are discussed. |
| Keywords: | cyclic sulfoxide metallation reactions stereochemistry aromatic aldehydes |
| 本文献已被 ScienceDirect 等数据库收录！ | |