An efficient [4 + 2 + 1] entry to seven-membered rings

Journal of the American Chemical Society
Yike Ni, John Montgomery

Abstract

A new nickel-catalyzed procedure for the [4 + 2 + 1] cycloaddition of trimethylsilyl diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Three possible mechanisms are proposed, and each involves the generation of a transient nickel carbene species.

References

Oct 3, 1999·Angewandte Chemie·H J KnölkerO Spieß
Jul 13, 2000·The Journal of Organic Chemistry·H M DaviesR M Churchill
Mar 21, 2002·Journal of the American Chemical Society·Paul A WenderLei Zhang
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Citations

Feb 24, 2006·Journal of the American Chemical Society·Yike Ni, John Montgomery
May 3, 2011·Journal of the American Chemical Society·Puneet KumarJanis Louie
Jun 22, 2012·Organic Letters·Min JiangJan-E Bäckvall
Apr 26, 2017·The Journal of Organic Chemistry·Junxiang MinJiangtao Sun
Nov 11, 2014·Organic & Biomolecular Chemistry·Ryosuke HaraguchiSeijiro Matsubara
Oct 19, 2007·Angewandte Chemie·Alois Fürstner, Christopher C Stimson
Apr 3, 2008·Angewandte Chemie·Véronique MicheletJean-Pierre Genêt
Mar 7, 2020·Chemistry : a European Journal·Damián PadínCarlos Saá
Apr 12, 2013·Chemistry : a European Journal·Min Jiang, Jan-E Bäckvall
Jan 21, 2020·Chemical Society Reviews·Dong ZhuShifa Zhu
Oct 21, 2015·Angewandte Chemie·Naijing SuTom G Driver
Nov 6, 2018·Organic & Biomolecular Chemistry·Chao PeiXinfang Xu
Jul 27, 2020·Chemistry : a European Journal·Barry M TrostJohnathan E Schultz
Dec 31, 2020·Chemistry : a European Journal·Qi CuiZhi-Xiang Yu
Apr 21, 2005·Journal of the American Chemical Society·Gang Zuo, Janis Louie
Oct 26, 2010·Organic Letters·Yoshiaki TakadaSeijiro Matsubara
May 19, 2005·Journal of the American Chemical Society·Sze-Sze Ng, Timothy F Jamison

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