Literature DB >> 22847823

Gold-catalyzed one-step construction of 2,3-dihydro-1H-Pyrrolizines with an electron-withdrawing group in the 5-position: a formal synthesis of 7-methoxymitosene.

Ze-Yi Yan1, Yuanjing Xiao, Liming Zhang.   

Abstract

What a ring formation! Bicyclic dihydropyrrolizines with an electron-withdrawing group (EWG) at the 5-position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically-controlled regioselectivity, and the generation of destabilized 1-azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7-methoxymitosene.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22847823     DOI： 10.1002/anie.201203678

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


  10 in total

Review 1.  5-Endo-dig cyclizations in organic syntheses.

Authors:  Muhammad Aamir Sajid; Zulfiqar Ali Khan; Sohail Anjum Shahzad; Syed Ali Raza Naqvi; Muhammad Usman
Journal:  Mol Divers       Date:  2019-03-05       Impact factor: 2.943

2.  One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade.

Authors:  Zhitong Zheng; Huangfei Tu; Liming Zhang
Journal:  Chemistry       Date:  2014-01-30       Impact factor: 5.236

3.  A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes.

Authors:  Hongyi Chen; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-12       Impact factor: 15.336

4.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

5.  Gold carbene or carbenoid: is there a difference?

Authors:  Yahui Wang; Michael E Muratore; Antonio M Echavarren
Journal:  Chemistry       Date:  2015-03-18       Impact factor: 5.236

6.  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

7.  Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles.

Authors:  Ai-Hua Zhou; Qiao He; Chao Shu; Yong-Fei Yu; Shuang Liu; Tian Zhao; Wei Zhang; Xin Lu; Long-Wu Ye
Journal:  Chem Sci       Date:  2014-11-12       Impact factor: 9.825

8.  Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes.

Authors:  Yuiki Kawada; Shunsuke Ohmura; Misaki Kobayashi; Wataru Nojo; Masaki Kondo; Yuka Matsuda; Junpei Matsuoka; Shinsuke Inuki; Shinya Oishi; Chao Wang; Tatsuo Saito; Masanobu Uchiyama; Takanori Suzuki; Hiroaki Ohno
Journal:  Chem Sci       Date:  2018-09-10       Impact factor: 9.825

Review 9.  Computational protein engineering: bridging the gap between rational design and laboratory evolution.

Authors:  Alexandre Barrozo; Rok Borstnar; Gaël Marloie; Shina Caroline Lynn Kamerlin
Journal:  Int J Mol Sci       Date:  2012-09-28       Impact factor: 5.923

10.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336
  10 in total

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