Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform

Journal of the American Chemical Society
Kenichiro ItamiJun-ichi Yoshida

Abstract

We have developed a programmable and diversity-oriented synthetic scheme for tetrasubstituted olefins through a site-selective and sequential assembly of pi-components onto a C=C core of vinyl 2-pyrimidyl sulfide. Noteworthy features are that (i) all components assembled stem from readily available organic halides or their Grignard reagents, (ii) the installation at the desired position can be achieved by the addition of the components in the appropriate order, and (iii) simple alteration of addition order in the sequence results in the production of all possible regio- and stereoisomers of multisubstituted olefins.

References

Jul 19, 2001·Journal of the American Chemical Society·A F Littke, G C Fu

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Citations

Mar 25, 2005·Organic Letters·Kenichiro ItamiJun-ichi Yoshida
Oct 21, 2005·Organic Letters·Zenichi IkedaSeijiro Matsubara
Oct 18, 2011·Organic Letters·Andrew J EberhartDavid J Procter
Jun 25, 2013·Organic Letters·Fei ZhaoZhang-Jie Shi
May 8, 2014·Organic Letters·Jie Tang, Lukas J Goossen
Aug 23, 2016·Journal of the American Chemical Society·Jennifer L KennemurKami L Hull
Oct 7, 2016·Chemical Communications : Chem Comm·Jia YangLi-Biao Han
Jun 21, 2011·Angewandte Chemie·Takehisa MaekawaKenichiro Itami
Oct 5, 2017·Angewandte Chemie·Shin SuzukiJunichiro Yamaguchi
Dec 29, 2005·Chemistry : a European Journal·Kenichiro Itami, Jun-ichi Yoshida
Oct 20, 2012·Chemical Society Reviews·Liandi WangZhengkun Yu
Jun 23, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Masayuki Iwasaki, Yasushi Nishihara
Jan 7, 2021·Chemical Society Reviews·Marzieh AhangarpourMargaret A Brimble
Mar 27, 2020·ChemSusChem·Sudripet SharmaSachin Handa
Mar 20, 2009·Organic Letters·Jérôme CanivetKenichiro Itami
Nov 2, 2007·Chemical Reviews·Alison B Flynn, William W Ogilvie
Mar 25, 2005·The Journal of Organic Chemistry·Kenichiro ItamiJun-ichi Yoshida
Jul 21, 2017·Organic Letters·Louis Jeanne-JulienEmmanuel Roulland

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