Lewis acid-promoted cyclization/halogenation of allenyl ethenetricarboxylates and the corresponding amides: stereoselective synthesis of haloalkenyl five-membered heterocycles

Lewis acid-promoted intramolecular reactions of allenyl ethenetricarboxylates and the corresponding amides have been examined. Reactions of allenyl ethenetricarboxylates and the amides with Lewis acids such as AlCl3, AlBr3 and ZnX2 (X = Cl, Br, I) gave 3,4-trans haloalkenyl five-membered heterocycle...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 12; no. 23; pp. 3964 - 3975
Main Authors Fukushima, Yugo, Yamazaki, Shoko, Ogawa, Akiya
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.06.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
ARYLATIVE CYCLIZATION
CYCLIZATION REACTIONS
INTRAMOLECULAR HYDROARYLATION
Online AccessGet full text

Cover

More Information
Summary:Lewis acid-promoted intramolecular reactions of allenyl ethenetricarboxylates and the corresponding amides have been examined. Reactions of allenyl ethenetricarboxylates and the amides with Lewis acids such as AlCl3, AlBr3 and ZnX2 (X = Cl, Br, I) gave 3,4-trans haloalkenyl five-membered heterocycles stereoselectively. The stereochemistry was determined by NOE experiments and reduction of the cyclized products. Various transformations of the haloalkenyl functionalized cyclic compounds have also been performed.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00233d