Reactivity of chiral alpha-amidoalkylphenyl sulfones with stabilized carbanions. stereoselective synthesis of optically active 1-aminopyrrolizidine |
| |
Authors: | Giri Nicola Petrini Marino Profeta Roberto |
| |
Institution: | Dipartimento di Scienze Chimiche, Università di Camerino, via S. Agostino, 1, I-62032 Camerino, Italy. |
| |
Abstract: | Metal enolates and functionalized allylzinc reagents react with optically active alpha-amidoalkylphenyl sulfones to give N-carbamoylamino derivatives with variable levels of anti diastereoselectivity. Zinc enolates provide comparable results with respect to lithium enolates in terms of diastereoselectivity but afford beta-amino ester derivatives in lower yield. The synthetic utility of the obtained chiral N-carbamoylamino esters is demonstrated by the first enantioselective synthesis of (-)-1-aminopyrrolizidine a central intermediate for the preparation of various biologically active substances. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|