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

^*Corresponding author for this work

Department of Pharmacy

Kyungpook National University
Dana-Farber Cancer Institute
Harvard University
CHA University
Seoul National University

Research output: Contribution to journal › 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 - 2018.11.19

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\}",

note = "Publisher Copyright: {\textcopyright} 2018 by the authors.",

year = "2018",

month = nov,

day = "19",

doi = "10.3390/molecules23113023",

language = "English",

volume = "23",

journal = "Molecules",

issn = "1420-3049",

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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 - https://www.scopus.com/pages/publications/85056958940

U2 - 10.3390/molecules23113023

DO - 10.3390/molecules23113023

M3 - Journal 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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