Literature DB >> 23701315

Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Renhe Liu1, Gabrielle N Winston-McPherson, Zhong-Yue Yang, Xin Zhou, Wangze Song, Ilia A Guzei, Xiufang Xu, Weiping Tang.   

Abstract

Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.

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Year:  2013        PMID： 23701315      PMCID： PMC3884031          DOI： 10.1021/ja4047069

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


  62 in total

1.  Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-03-20       Impact factor: 15.419

2.  Gold-catalyzed organic reactions.

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

3.  Gold-catalyzed oxidative cyclization of 1,5-enynes using external oxidants.

Authors:  Dhananjayan Vasu; Hsiao-Hua Hung; Sabyasachi Bhunia; Sagar Ashok Gawade; Arindam Das; Rai-Shung Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-06       Impact factor: 15.336

4.  An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation.

Authors:  Weimin He; Chaoqun Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

5.  Gold-catalyzed 1,2-difunctionalizations of aminoalkynes using only N- and O-containing oxidants.

Authors:  Anupam Mukherjee; Ramesh B Dateer; Rupsha Chaudhuri; Sabyasachi Bhunia; Somnath Narayan Karad; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2011-09-12       Impact factor: 15.419

6.  A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes.

Authors:  Longwu Ye; Weimin He; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-04       Impact factor: 15.336

7.  Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

Authors:  Longwu Ye; Li Cui; Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

8.  Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles.

Authors:  Hyun-Suk Yeom; Youngun Lee; Ji-Eun Lee; Seunghoon Shin
Journal:  Org Biomol Chem       Date:  2009-09-01       Impact factor: 3.876

Review 9.  Application of donor/acceptor-carbenoids to the synthesis of natural products.

Authors:  Huw M L Davies; Justin R Denton
Journal:  Chem Soc Rev       Date:  2009-09-30       Impact factor: 54.564

10.  New Fischer carbene complexes of rhodium(i): preparation and 2-cyclopentenone ring synthesis by annelation to alkynes.

Authors:  José Barluenga; Rubén Vicente; Luis A López; Eduardo Rubio; Miguel Tomás; Carmen Alvarez-Rúa
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419
View more
  7 in total

1.  Ynamides in ring forming transformations.

Authors:  Xiao-Na Wang; Hyun-Suk Yeom; Li-Chao Fang; Shuzhong He; Zhi-Xiong Ma; Brant L Kedrowski; Richard P Hsung
Journal:  Acc Chem Res       Date:  2013-10-28       Impact factor: 22.384

2.  Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides.

Authors:  Holly V Adcock; Elli Chatzopoulou; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-30       Impact factor: 15.336

3.  Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

Authors:  Wen-Bo Shen; Qing Sun; Long Li; Xin Liu; Bo Zhou; Juan-Zhu Yan; Xin Lu; Long-Wu Ye
Journal:  Nat Commun       Date:  2017-11-23       Impact factor: 14.919

4.  Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.

Authors:  Quynh H Nguyen; Nguyen H Nguyen; Hanbyul Kim; Seunghoon Shin
Journal:  Chem Sci       Date:  2019-08-12       Impact factor: 9.825

5.  Divergent ynamide reactivity in the presence of azides - an experimental and computational study.

Authors:  Veronica Tona; Stefan A Ruider; Martin Berger; Saad Shaaban; Mohan Padmanaban; Lan-Gui Xie; Leticia González; Nuno Maulide
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825

6.  A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides.

Authors:  Fernando Sánchez-Cantalejo; Joshua D Priest; Paul W Davies
Journal:  Chemistry       Date:  2018-10-30       Impact factor: 5.236

7.  Gold(I)-Catalyzed Aromatization: Expeditious Synthesis of Polyfunctionalized Naphthalenes.

Authors:  Cheng Zhang; Kemiao Hong; Shanliang Dong; Chao Pei; Xiaolu Zhang; Ciwang He; Wenhao Hu; Xinfang Xu
Journal:  iScience       Date:  2019-10-25
  7 in total

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