Literature DB >> 18576648

Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation.

Nathan D Shapiro1, F Dean Toste.   

Abstract

A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate.

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Year:  2008        PMID： 18576648      PMCID： PMC2754784          DOI： 10.1021/ja803890t

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


  20 in total

1.  Molecular diversity through gold catalysis with alkynes.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Commun (Camb)       Date:  2006-11-09       Impact factor: 6.222

2.  Gold(I)-catalyzed oxidative rearrangements.

Authors:  Cole A Witham; Pablo Mauleón; Nathan D Shapiro; Benjamin D Sherry; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-04-14       Impact factor: 15.419

Review 3.  Relativistic effects in homogeneous gold catalysis.

Authors:  David J Gorin; F Dean Toste
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

4.  Golden carousel in catalysis: the cationic gold/propargylic ester cycle.

Authors:  Andrea Correa; Nicolas Marion; Louis Fensterbank; Max Malacria; Steven P Nolan; Luigi Cavallo
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

6.  Au-containing all-carbon 1,4-dipoles: generation and [4 + 2] annulation in the formation of carbo-/heterocycles.

Authors:  Guozhu Zhang; Xiaogen Huang; Guotao Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2008-01-19       Impact factor: 15.419

7.  Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Authors:  Magnus J Johansson; David J Gorin; Steven T Staben; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

8.  Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors:  Koji Miki; Kouichi Ohe; Sakae Uemura
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

9.  Gold-catalyzed [4+3]-annulation of oxabicyclic benzenes with 2-substituted allylsilanes through tandem allylation and cyclization.

Authors:  Yu-Chia Hsu; Swarup Datta; Chun-Ming Ting; Rai-Shung Liu
Journal:  Org Lett       Date:  2008-01-10       Impact factor: 6.005

10.  Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes.

Authors:  David J Gorin; Iain D G Watson; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419
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  19 in total

1.  Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.

Authors:  Cristina Navarro; Nathan D Shapiro; Maurizio Bernasconi; Takahiro Horibe; F Dean Toste
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

2.  Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

Authors:  Li Cui; Longwu Ye; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-03-30       Impact factor: 6.222

3.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

4.  Gold-catalyzed Intermolecular [4C + 3C] Cycloaddition Reactions.

Authors:  Benjamin W Gung; Lauren N Bailey; Josh Wonser
Journal:  Tetrahedron Lett       Date:  2010-04-28       Impact factor: 2.415

5.  Development of an automated microfluidic reaction platform for multidimensional screening: reaction discovery employing bicyclo[3.2.1]octanoid scaffolds.

Authors:  John R Goodell; Jonathan P McMullen; Nikolay Zaborenko; Jason R Maloney; Chuan-Xing Ho; Klavs F Jensen; John A Porco; Aaron B Beeler
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

Review 6.  Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors:  Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal:  Chem Soc Rev       Date:  2012-12-07       Impact factor: 54.564

7.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

8.  Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates.

Authors:  Minoru Uemura; Iain D G Watson; Mikimoto Katsukawa; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-03-18       Impact factor: 15.419

9.  Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

Authors:  Pablo Mauleón; Jamin L Krinsky; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

10.  Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Authors:  Nathan D Shapiro; Yun Shi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419
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