Design and reactivity of topologically unique, chiral phosphonamides. Remarkable diastereofacial selectivity in asymmetric olefination and alkylation

S Hanessian, D Delorme, S Beaudoin…

文献索引：Hanessian, Stephen; Delorme, D.; Beaudoin, S.; Leblanc, Y. Journal of the American Chemical Society, 1984 , vol. 106, # 19 p. 5754 - 5756

全文：HTML全文

被引用次数: 140

摘要

The reaction leading to the formation of the imine probably proceeds via nucleophilic addition to the heteroatom, creating a highly stabilized cyclopentadienyl anion. The intermediate anion then undergoes elimination of the tosylate. The only significant side reaction appears to be reduction of the imine tosylate to the unsubstituted imine (vide infra). One possible means of eliminating this problem may be substituting a different carbanion ...