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Conversion of Medium-Sized Lactams to ?-Vinyl or ?-Acetylenyl Azacycles via N,O-Acetal TMS Ethers.


ABSTRACT: ?-Vinyl or ?-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.

SUBMITTER: Kim M 

PROVIDER: S-EPMC6278647 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via <i>N</i>,<i>O</i>-Acetal TMS Ethers.

Kim Minjun M   Jang Jaebong J   Choi Goyoung G   Chung Sungkyun S   Lim Changjin C   Hur Joonseong J   Kim Hyun Su HS   Na Younghwa Y   Son Woo Sung WS   Suh Young-Ger YG   Jung Jong-Wha JW   Kim Seok-Ho SH  

Molecules (Basel, Switzerland) 20181119 11


α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via <i>N</i>,<i>O</i>-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective <i>N</i>-acyliminium ion vinylation and acetylenylation intermediates generated from <i>N</i>,<i>O</i>-acetal TMS ethers in the presence of a Lewis acid. ...[more]

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