92695-14-2Relevant academic research and scientific papers
On the use of C2-symmetric aziridines as chiral auxiliaries
Tanner,Birgersson,Gogoll,Luthman
, p. 9797 - 9824 (2007/10/02)
A systematic study has been made of the utility of readily available C2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the axuiliaries can be cleaved off non-destructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.
Nucleophilic Participation of Phenyl in the Ring-Opening Reaction of cis- and trans-2,3-Dibenzyloxirane
Crotti, Paolo,Ferretti, Maria,Macchia, Franco,Stoppioni, Annalisa
, p. 4706 - 4711 (2007/10/02)
Methanolysis reactions of both epoxides cis-4 and trans-5 under different conditions are completely anti stereoselective, no trace of the products arising from syn opening being found.Also the hydrolysis, the acetolysis, and the trichloroacetolysis in non
