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Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers
α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation int...
| Autores principales: | , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
MDPI
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278647/ https://www.ncbi.nlm.nih.gov/pubmed/30463260 http://dx.doi.org/10.3390/molecules23113023 |
| _version_ | 1783378405243224064 |
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| author | Kim, Minjun Jang, Jaebong Choi, Goyoung Chung, Sungkyun Lim, Changjin Hur, Joonseong Kim, Hyun Su Na, Younghwa Son, Woo Sung Suh, Young-Ger Jung, Jong-Wha Kim, Seok-Ho |
| author_facet | Kim, Minjun Jang, Jaebong Choi, Goyoung Chung, Sungkyun Lim, Changjin Hur, Joonseong Kim, Hyun Su Na, Younghwa Son, Woo Sung Suh, Young-Ger Jung, Jong-Wha Kim, Seok-Ho |
| author_sort | Kim, Minjun |
| collection | PubMed |
| description | α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid. |
| format | Online Article Text |
| id | pubmed-6278647 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | MDPI |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-62786472018-12-13 Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers Kim, Minjun Jang, Jaebong Choi, Goyoung Chung, Sungkyun Lim, Changjin Hur, Joonseong Kim, Hyun Su Na, Younghwa Son, Woo Sung Suh, Young-Ger Jung, Jong-Wha Kim, Seok-Ho Molecules Article α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid. MDPI 2018-11-19 /pmc/articles/PMC6278647/ /pubmed/30463260 http://dx.doi.org/10.3390/molecules23113023 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Article Kim, Minjun Jang, Jaebong Choi, Goyoung Chung, Sungkyun Lim, Changjin Hur, Joonseong Kim, Hyun Su Na, Younghwa Son, Woo Sung Suh, Young-Ger Jung, Jong-Wha Kim, Seok-Ho Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers |
| title | Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers |
| title_full | Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers |
| title_fullStr | Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers |
| title_full_unstemmed | Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers |
| title_short | Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers |
| title_sort | conversion of medium-sized lactams to α-vinyl or α-acetylenyl azacycles via n,o-acetal tms ethers |
| topic | Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278647/ https://www.ncbi.nlm.nih.gov/pubmed/30463260 http://dx.doi.org/10.3390/molecules23113023 |
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