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; Young Ger Suh

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, Young Ger Suh

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4 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	886-899
Number of pages	14
Journal	Heterocycles
Volume	92
Issue number	5
DOIs	https://doi.org/10.3987/COM-16-13432
State	Published - 2016

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title = "Studies on the aza-Claisen rearrangement of 7 to 9-membered vinylazacycles",

abstract = "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.",

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AU - Kim, Seok Ho

AU - Lee, Won Il

AU - Kim, Seon Mi

AU - Jung, Jae Kyung

AU - Jang, Jaebong

AU - Sim, Jaehoon

AU - Jung, Jong Wha

AU - Suh, Young Ger

PY - 2016

Y1 - 2016

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AB - 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.

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Studies on the aza-Claisen rearrangement of 7 to 9-membered vinylazacycles

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