Role of the gem-difluoro moiety in the tandem ring-closing metathesis-olefin isomerization:: Regioselective preparation of unsaturated lactams

被引：88
作者：
Fustero, S [1 ]
Sánchez-Roselló, M
Jiménez, D
Sanz-Cervera, JF
del Pozo, C
Aceña, JL
机构：
[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
[2] Ctr Invest Principe Felipe, Lab Mol Organ, E-46013 Valencia, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 07期
关键词：
D O I：
10.1021/jo0525635
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Careful selection of the metathesis catalyst, solvent, and reaction conditions allows for the efficient and regioselective synthesis of isomeric fluorinated and nonfluorinated lactam derivatives II and III from precursor amides I through a ring-closing metathesis (RCM) reaction or a tandem RCM-isomerization protocol, respectively. The presence of the gem-difluoro moiety in the starting materials exerts a pivotal effect by directing the isomerization step, making the overall tandem transformation a regioselective process. The scope, limitations, and synthetic usefulness of this protocol are also discussed.
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页码：2706 / 2714
页数：9
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