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Paper | Regular issue | Vol 92, No. 5, 2016, pp.886-899
Published online, 24th March, 2016
DOI: 10.3987/COM-16-13432
Studies on the aza-Claisen Rearrangement of 7 to 9-Membered Vinylazacycles

Seok-Ho Kim, Won-Il Lee, Seon-Mi Kim, Jae-Kyung Jung, Jaebong Jang, Jaehoon Sim, Jong-Wha Jung,* and Young-Ger Suh*

*Department of Pharmacy, Kyungpook National University, #411 80 Daehak-ro Buk-gu 41566, Korea


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 α-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.