One-pot synthesis of novel enantiomerically pure and racemic 4-ferrocenyl-β-lactams and their reactivity in acidic media

被引：15
作者：
Bernardi, L [1 ]
Bonini, BF [1 ]
Comes-Franchini, M [1 ]
Dessole, G [1 ]
Fochi, M [1 ]
Ricci, A [1 ]
机构：
[1] Univ Bologna, Fac Chim Ind, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 15期
关键词：
lactams; ferrocene; chirality; carbocations;
D O I：
10.1002/ejoc.200500170
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 4-ferrocenyl- and 4-[(S-FC)-2-(p-tolylsulfanyl)ferrocenyl)-beta-lactams has been synthesized in good yields by a one-pot reaction of achiral and planar-chiral ferrocenylimines with substituted acetic acids. The acid-induced stereoconvergent transformation of cis- and trans-4-ferrocenyl-beta-lactams into (Z)-alpha,beta-unsaturated amides by protonation, NC-4 cleavage and subsequent exo-H elimination and the lack of reaction of the ortho-S-tolylsulfanyl analogs are discussed. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码：3326 / 3333
页数：8
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