Literature DB >> 15070365

Copper-catalyzed tandem conjugate addition-electrophilic trapping: ketones, esters, and nitriles as terminal electrophiles.

Kyriacos Agapiou1, David F Cauble, Michael J Krische.   

Abstract

Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition-electrophilic trapping.

Entities:  

Year:  2004        PMID: 15070365     DOI: 10.1021/ja030603l

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

Authors:  Venukrishnan Komanduri; Fernando Pedraza; Michael J Krische
Journal:  Adv Synth Catal       Date:  2008-07-07       Impact factor: 5.837

2.  (+)-Sorangicin A: evolution of a viable synthetic strategy.

Authors:  Amos B Smith; Shuzhi Dong; Richard J Fox; Jehrod B Brenneman; John A Vanecko; Tomohiro Maegawa
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

3.  Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.

Authors:  Yuyang Dong; Alexander W Schuppe; Binh Khanh Mai; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2022-03-26       Impact factor: 16.383

4.  Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.

Authors:  Nathan R Cichowicz; Will Kaplan; Yaroslav Khomutnyk; Bijay Bhattarai; Zhankui Sun; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

5.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

  5 in total

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