Stereospecific cyclization reaction of alkenyl esters and amides of ethenetricarboxylate-Reference-Cited by-同舟云学术

Stereospecific cyclization reaction of alkenyl esters and amides of ethenetricarboxylate

Published:2015-10 Issue:10 Volume:93 Page:1122-1131
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Yamazaki Shoko¹,Wada Junya¹,Kakiuchi Kiyomi²

Affiliation:

1. Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan.

2. Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan.

Abstract

The stereospecificity of the cyclization reaction of (E)- and (Z)-2-alkenyl esters and amides of ethenetricarboxylate has been examined. The reaction of (E)/(Z)-2-butenyl esters with AlCl3 or FeCl3 gave trans-substituted chlorinated γ-lactone diastereomers stereospecifically. (E)/(Z)-2-butenyl and pentenyl amides undergo an intramolecular ene reaction at room temperature gradually. At 80 °C, the (Z)-alkenyl amides were transformed to cis-substituted ene adducts and the (E)-amides were transformed to cis- and trans-substituted ene adduct mixtures. The reaction of (E)/(Z)-2-alkenyl amides with ZnI2 gave trans-substituted γ-lactam diastereomers stereospecifically along with the ene adducts.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/cjc-2015-0129

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