Literature DB >> 26609195

Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.

Yuji Matsushima1, Eric M Phillips1, Robert G Bergman2, Jonathan A Ellman1.   

Abstract

A new and unexpected Rh(I)-catalyzed cycloisomerization of 1,6-enynes is reported. Several different alkyne substitution patterns were evaluated under the reaction conditions, including a deuterated derivative that provides some insight into the reaction mechanism.

Entities:  

Keywords:  enones; homogeneous catalysis; isomerization; rhodium; ring closure

Year:  2015        PMID: 26609195      PMCID: PMC4655000          DOI: 10.1055/s-0034-1380359

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  25 in total

1.  A versatile new method for the synthesis of cyclopentenones via an unusual rhodium-catalyzed intramolecular trans hydroacylation of an alkyne.

Authors:  K Tanaka; G C Fu
Journal:  J Am Chem Soc       Date:  2001-11-21       Impact factor: 15.419

2.  Stereoselective alkylation of alpha,beta-unsaturated imines via C-H bond activation.

Authors:  Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2006-05-03       Impact factor: 15.419

3.  Gold(I)-catalyzed cyclizations of 1,6-enynes: alkoxycyclizations and exo/endo skeletal rearrangements.

Authors:  Cristina Nieto-Oberhuber; M Paz Muñoz; Salomé López; Eloísa Jiménez-Núñez; Cristina Nevado; Elena Herrero-Gómez; Mihai Raducan; Antonio M Echavarren
Journal:  Chemistry       Date:  2006-02-08       Impact factor: 5.236

4.  Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.

Authors:  Jung Min Joo; Ramoncito A David; Yu Yuan; Chulbom Lee
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

5.  Synthesis of monoalkoxide monopyrrolyl complexes Mo(NR)(CHR')(OR'')(pyrrolyl): enyne metathesis with high oxidation state catalysts.

Authors:  Rojendra Singh; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

6.  The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization.

Authors:  Sirilata Yotphan; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-02-05       Impact factor: 15.419

7.  Rhodium-catalyzed cascade reactions of dienynes leading to substituted dihydronaphthalenes and naphthalenes.

Authors:  Eri Okazaki; Ryuichi Okamoto; Yu Shibata; Keiichi Noguchi; Ken Tanaka
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-24       Impact factor: 15.336

8.  Highly functionalized pyridines synthesis from N-sulfonyl ketimines and alkynes using the N-S bond as an internal oxidant.

Authors:  Qian-Ru Zhang; Ji-Rong Huang; Wei Zhang; Lin Dong
Journal:  Org Lett       Date:  2014-03-05       Impact factor: 6.005

9.  Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Authors:  Simon Duttwyler; Shuming Chen; Colin Lu; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-06       Impact factor: 15.336

10.  Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.

Authors:  Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-12-18       Impact factor: 15.419

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