STUDIES ON THE AZA-CLAISEN REARRANGEMENT OF 7 TO 9-MEMBERED VINYLAZACYCLES

A systematic study on the amide enolate-induced aza-Claisen rearrangement (ACR) of 7 to 9-membered vinylazacycles has been carried out, resulting in an efficient synthetic method to prepare 11 to 13-membered macrolactams. Key feature includes introduction of electron-donating substituents at a-posit...

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Bibliographic Details
Published inHeterocycles Vol. 92; no. 5; pp. 886 - 899
Main Authors Kim, Seok-Ho, Lee, Won-Il, Kim, Seon-Mi, Jung, Jae-Kyung, Jang, Jaebong, Sim, Jaehoon, Jung, Jong-Wha, Suh, Young-Ger
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.05.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MACROLACTAMS
LACTAMS
RING-CLOSING METATHESIS
DERIVATIVES
STRATEGY
VINYL ETHERS
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Summary:A systematic study on the amide enolate-induced aza-Claisen rearrangement (ACR) of 7 to 9-membered vinylazacycles has been carried out, resulting in an efficient synthetic method to prepare 11 to 13-membered macrolactams. Key feature includes introduction of electron-donating substituents at a-position of the amide substrates possessing 7 to 9-membered vinylazacycles to facilitate amide enolate-induced.ACR. In addition, substituent effects on ACR has been discussed based on the experimental results. We believe this study would provide experimental evidences for the substituent effects and envision for the synthetic application of ACR-induced ring expansion.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-16-13432