Gold catalysis: tandem reactions of diyne-diols and external nucleophiles as an easy access to tricyclic cage-like structures

Chemistry : a European Journal
A Stephen K HashmiWolfgang Frey

Abstract

Different diyne-diols composed of two terminal homopropargylic alcohol groups were prepared by bi-directional synthesis. Subjection of the syn diastereomers to NAC-gold catalysts (NAC=nitrogen acyclic carbene) in the presence of external nucleophiles such as water or anilines provided substituted and highly rigid heterocyclic cages. The corresponding anti disastereomers polymerised. An intermediate of the reactions of the syn diastereomers could be isolated and even be characterised by crystal structure analysis. Overall, eight new bonds are formed in the reaction, which proceeds by a multistep sequence of highly selective hydroalkoxylations and hydrohydroxylation or hydroaminations. For furyl substituents and for internal alkynes competing reaction pathways could be identified. By the cross-coupling of a product with an iodoaryl substituent, the use of these cage compounds as geometrically defined linking groups by using orthogonal transition-metal-catalysed methodology, namely, gold and palladium catalysis, could be demonstrated.

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Citations

Feb 15, 2017·Angewandte Chemie·Thomas WurmA Stephen K Hashmi
Jan 27, 2018·Chemistry : a European Journal·Vanessa WeingandA Stephen K Hashmi
Oct 6, 2017·Chemistry, an Asian Journal·Yi-Jhen FengYing-Chih Lin
Sep 22, 2010·Chemical Communications : Chem Comm·Ayhan S DemirKerem Buran
Jun 14, 2012·Chemical Communications : Chem Comm·Ramesh B DateerRai-Shung Liu
Nov 10, 2011·Chemistry : a European Journal·María Martín-RodríguezFernando P Cossío
Feb 9, 2012·Chemical Communications : Chem Comm·Naoki AsaoAkihisa Inoue
Nov 20, 2012·Chemical Communications : Chem Comm·John M KetchamAaron Aponick
Apr 8, 2015·Chemical Communications : Chem Comm·Justin A Goodwin, Aaron Aponick
Dec 21, 2011·Chemical Society Reviews·Matthias Rudolph, A Stephen K Hashmi
Apr 14, 2011·Organic & Biomolecular Chemistry·Benito AlcaideJosé Miguel Alonso
May 5, 2012·Chemistry : a European Journal·Andrew J AtkinsMatthias Bauer
Nov 15, 2011·Angewandte Chemie·Ramesh B DateerRai-Shung Liu
Jun 15, 2011·Angewandte Chemie·David LebœufLouis Fensterbank
Apr 1, 2011·Chemical Communications : Chem Comm·Matthias Rudolph, A Stephen K Hashmi
Jun 2, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Chandrasekar Praveen
Jun 2, 2021·Organic & Biomolecular Chemistry·Guang-Xin RuGuang-Qin Gao
Jul 15, 2021·Chemical Reviews·Alba ColladoSteven P Nolan
Oct 24, 2012·Organic Letters·Sabyasachi BhuniaRai-Shung Liu
Jan 17, 2014·Accounts of Chemical Research·Benito Alcaide, Pedro Almendros
May 1, 2013·Journal of the American Chemical Society·Weidong RaoPhilip Wai Hong Chan
Sep 22, 2017·Inorganic Chemistry·Ashwin G NairBarbara A Messerle
Apr 23, 2013·Organic Letters·Xianghua WangZhenghu Xu
Dec 11, 2013·Organic Letters·Xianghua WangZhenghu Xu

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