Literature DB >> 24150975

Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.

Xing-Zhong Shu1, Casi M Schienebeck, Wangze Song, Ilia A Guzei, Weiping Tang.   

Abstract

Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  catalysis; enynes; polycyclic compounds; rhodium; stereospecific reactions

Mesh：

Substances：

Year:  2013        PMID： 24150975      PMCID： PMC3867534          DOI： 10.1002/anie.201306919

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  47 in total

1.  The first intermolecular transition metal-catalyzed [5+2] cycloadditions with simple, unactivated, vinylcyclopropanes.

Authors:  P A Wender; C M Barzilay; A J Dyckman
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Review 2.  A fresh look at natural tropolonoids.

Authors:  Ronald Bentley
Journal:  Nat Prod Rep       Date:  2007-11-22       Impact factor: 13.423

3.  Selectivity in nickel-catalyzed rearrangements of cyclopropylen-ynes.

Authors:  Gang Zuo; Janis Louie
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

4.  Mechanism and origins of ligand-controlled selectivities in [Ni(NHC)]-catalyzed intramolecular (5 + 2) cycloadditions and homo-ene reactions: a theoretical study.

Authors:  Xin Hong; Peng Liu; K N Houk
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

5.  Syntheses of seven-membered rings: ruthenium-catalyzed intramolecular [5+2] cycloadditions.

Authors:  Barry M Trost; Hong C Shen; Daniel B Horne; F Dean Toste; Bernhard G Steinmetz; Christopher Koradin
Journal:  Chemistry       Date:  2005-04-08       Impact factor: 5.236

6.  Reaction of alpha-ene-vinylcyclopropanes: type II intramolecular [5+2] cycloaddition or [3+2] cycloaddition?

Authors:  Qian Li; Guo-Jie Jiang; Lei Jiao; Zhi-Xiang Yu
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

7.  Asymmetric organocatalysis of 4 + 3 cycloaddition reactions.

Authors:  Michael Harmata; Sunil K Ghosh; Xuechuan Hong; Sumrit Wacharasindhu; Patrick Kirchhoefer
Journal:  J Am Chem Soc       Date:  2003-02-26       Impact factor: 15.419

8.  An atom-economic synthesis of bicyclo[3.1.0]hexanes by rhodium N-heterocyclic carbene-catalyzed diastereoselective tandem hetero-[5+2] cycloaddition/Claisen rearrangement reaction of vinylic oxiranes with alkynes.

Authors:  Jian-Jun Feng; Junliang Zhang
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

9.  A computationally designed Rh(I)-catalyzed two-component [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of cyclooctenones.

Authors:  Yuanyuan Wang; Jingxin Wang; Jiachun Su; Feng Huang; Lei Jiao; Yong Liang; Dazhi Yang; Shiwei Zhang; Paul A Wender; Zhi-Xiang Yu
Journal:  J Am Chem Soc       Date:  2007-07-27       Impact factor: 15.419

10.  A cheap metal for a "noble" task: preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes.

Authors:  Alois Fürstner; Keisuke Majima; Rubén Martín; Helga Krause; Egmont Kattnig; Richard Goddard; Christian W Lehmann
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419
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  9 in total

1.  Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

Authors:  Xiaoxun Li; Hui Li; Wangze Song; Po-Sen Tseng; Lingyan Liu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-07       Impact factor: 15.336

2.  Catalytic Efficiency Is a Function of How Rhodium(I) (5 + 2) Catalysts Accommodate a Conserved Substrate Transition State Geometry: Induced Fit Model for Explaining Transition Metal Catalysis.

Authors:  Thomas J L Mustard; Paul A Wender; Paul Ha-Yeon Cheong
Journal:  ACS Catal       Date:  2015-03-06       Impact factor: 13.084

3.  Gold(I)-catalyzed dearomative Rautenstrauch rearrangement: enantioselective access to cyclopenta[b]indoles.

Authors:  Weiwei Zi; Hongmiao Wu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-24       Impact factor: 15.419

4.  Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

Authors:  Xiaoxun Li; Haibo Xie; Xiaoning Fu; Ji-Tian Liu; Hao-Yuan Wang; Bao-Min Xi; Peng Liu; Xiufang Xu; Weiping Tang
Journal:  Chemistry       Date:  2016-06-20       Impact factor: 5.236

5.  Synthesis of Substituted Tropones by Sequential Rh-Catalyzed [5+2] Cycloaddition and Elimination.

Authors:  Wangze Song; Bao-Min Xi; Ka Yang; Weiping Tang
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

6.  Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

Authors:  Xing-zhong Shu; Casi M Schienebeck; Xiaoxun Li; Xin Zhou; Wangze Song; Lianqing Chen; Ilia A Guzei; Weiping Tang
Journal:  Org Lett       Date:  2015-10-06       Impact factor: 6.005

7.  Rhodium-Catalyzed Intermolecular [5+1] and [5+2] Cycloadditions Using 1,4-Enynes with an Electron-Donating Ester on the 3-Position.

Authors:  Casi M Schienebeck; Wangze Song; Angela M Smits; Weiping Tang
Journal:  Synthesis (Stuttg)       Date:  2015-02-03       Impact factor: 3.157

Review 8.  Rhodium-Catalyzed (5 + 2) and (5 + 1) Cycloadditions Using 1,4-Enynes as Five-Carbon Building Blocks.

Authors:  Stephanie A Blaszczyk; Daniel A Glazier; Weiping Tang
Journal:  Acc Chem Res       Date:  2019-12-10       Impact factor: 22.384

9.  3-Acyloxy-1,4-enyne: a New Five-carbon Synthon for Rhodium-Catalyzed (5+2) Cycloadditions.

Authors:  Casi M Schienebeck; Xiaoxun Li; Xing-Zhong Shu; Weiping Tang
Journal:  Pure Appl Chem       Date:  2014-03-01       Impact factor: 2.453
  9 in total

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