Conversion of medium-sized lactams to α-vinyl or α-acetylenyl azacycles via N,O-acetal TMS ethers

Minjun Kim; Jaebong Jang; Goyoung Choi; Sungkyun Chung; Changjin Lim; Joonseong Hur; Hyun Su Kim; Younghwa Na; Woo Sung Son; Young Ger Suh; Jong Wha Jung; Seok Ho Kim

doi:10.3390/molecules23113023

Conversion of medium-sized lactams to α-vinyl or α-acetylenyl azacycles via N,O-acetal TMS ethers

Minjun Kim, Jaebong Jang, Goyoung Choi, Sungkyun Chung, Changjin Lim, Joonseong Hur, Hyun Su Kim, Younghwa Na, Woo Sung Son, Young Ger Suh, Jong Wha Jung, Seok Ho Kim

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

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.

Original language	English
Article number	3023
Journal	Molecules
Volume	23
Issue number	11
DOIs	https://doi.org/10.3390/molecules23113023
State	Published - 19 Nov 2018

Keywords

Amidoalkylation
Medium-sized lactam
Α-vinyl or α-acetylenyl azacycles

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10.3390/molecules23113023

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title = "Conversion of medium-sized lactams to α-vinyl or α-acetylenyl azacycles via N,O-acetal TMS ethers",

abstract = "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.",

keywords = "Amidoalkylation, Medium-sized lactam, Α-vinyl or α-acetylenyl azacycles",

author = "Minjun Kim and Jaebong Jang and Goyoung Choi and Sungkyun Chung and Changjin Lim and Joonseong Hur and Kim, {Hyun Su} and Younghwa Na and Son, {Woo Sung} and Suh, {Young Ger} and Jung, {Jong Wha} and Kim, {Seok Ho}",

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month = nov,

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doi = "10.3390/molecules23113023",

language = "English",

volume = "23",

journal = "Molecules",

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TY - JOUR

T1 - Conversion of medium-sized lactams to α-vinyl or α-acetylenyl azacycles via N,O-acetal TMS ethers

AU - Kim, Minjun

AU - Jang, Jaebong

AU - Choi, Goyoung

AU - Chung, Sungkyun

AU - Lim, Changjin

AU - Hur, Joonseong

AU - Kim, Hyun Su

AU - Na, Younghwa

AU - Son, Woo Sung

AU - Suh, Young Ger

AU - Jung, Jong Wha

AU - Kim, Seok Ho

PY - 2018/11/19

Y1 - 2018/11/19

N2 - 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.

AB - 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.

KW - Amidoalkylation

KW - Medium-sized lactam

KW - Α-vinyl or α-acetylenyl azacycles

UR - http://www.scopus.com/inward/record.url?scp=85056958940&partnerID=8YFLogxK

U2 - 10.3390/molecules23113023

DO - 10.3390/molecules23113023

M3 - Article

C2 - 30463260

AN - SCOPUS:85056958940

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 11

M1 - 3023

ER -

Conversion of medium-sized lactams to α-vinyl or α-acetylenyl azacycles via N,O-acetal TMS ethers

Abstract

Keywords

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