Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-Stetter/Paal-Knorr strategy

Organic Letters
Ashwin R Bharadwaj, Karl A Scheidt

Abstract

[reaction: see text] A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.

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Citations

Feb 16, 2012·Journal of the American Chemical Society·Yaojia JiangCheol-Min Park
Jun 11, 2011·Organic Letters·Benjamin B Thompson, John Montgomery
Oct 22, 2004·Organic Letters·Christopher T ClarkKarl A Scheidt
May 26, 2017·Organic & Biomolecular Chemistry·Qiao RenJian Wang
Aug 1, 2015·Chemical Communications : Chem Comm·Dipak Kumar TiwariPravin R Likhar
Sep 16, 2015·Organic & Biomolecular Chemistry·Ramachandra Reddy DonthiriSubbarayappa Adimurthy
Mar 10, 2007·Angewandte Chemie·Nicolas MarionSteven P Nolan
Jul 26, 2008·Chemical Communications : Chem Comm·Craig D CampbellAndrew D Smith
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Jun 21, 2011·Organic & Biomolecular Chemistry·Vijay NairEringathodi Suresh
Aug 15, 2013·Chemical Society Reviews·Hui-Jun ZhangCarsten Bolm
Aug 19, 2020·Chemical Communications : Chem Comm·Mingrui LiHe Huang
Jun 19, 2012·Angewandte Chemie·Jeremy FournierJanine Cossy
Jul 13, 2011·Organic & Biomolecular Chemistry·Chada Raji ReddyKothakonda Rajendra Prasad
Mar 17, 2012·Chemical Communications : Chem Comm·Xinxin QiCheol-Min Park
Aug 23, 2020·Materials·Krzysztof DzieszkowskiZbigniew Rafiński
Oct 10, 2008·Organic Letters·Yi-Feng WangKoichi Narasaka
Oct 25, 2007·Chemical Reviews·Dieter EndersAlexander Henseler
May 13, 2009·Organic Letters·Eugen MerkulThomas J J Müller

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