Literature DB >> 20668650

A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Hongyan Li1, Jennifer E Antoline, Jin-Haek Yang, Ziyad F Al-Rashid, Richard P Hsung.   

Abstract

This work describes the first examples of diastereoselective intramolecular cyclopropanations of a de novo class of push-pull carbenes derived from DMDO-epoxidations of chiral ynamides. This reaction sequence essentially constitutes a tandem epoxidation-cyclopropanation that effectively gives arise to a series of structurally unique amido-cyclopropanes. A plausible mechanistic model is proposed revealing insights into this novel cyclopropanation process.

Entities:  

Year:  2010        PMID： 20668650      PMCID： PMC2910449          DOI： 10.1039/c0nj00063a

Source DB:  PubMed          Journal:  New J Chem        ISSN： 1144-0546            Impact factor:   3.591


  33 in total

1.  First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant.

Authors:  Carole Alayrac; Dieter Schollmeyer; Bernhard Witulski
Journal:  Chem Commun (Camb)       Date:  2009-02-18       Impact factor: 6.222

2.  Atropisomerism of alpha,beta-unsaturated amidines: stereoselective synthesis by catalytic cascade reaction and optical resolution.

Authors:  Naoya Shindoh; Yoshiji Takemoto; Kiyosei Takasu
Journal:  Chemistry       Date:  2009-07-20       Impact factor: 5.236

3.  Creating aldols differently: how to build up aldol products with quaternary stereocenters starting from alkynes.

Authors:  Dennis C Koester; Daniel B Werz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Investigation into factors influencing stereoselectivity in the reactions of heterocycles with donor-acceptor-substituted rhodium carbenoids.

Authors:  Simon J Hedley; Dominic L Ventura; Paulina M Dominiak; Cara L Nygren; Huw M L Davies
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

5.  Synthesis of tricyclic fused 3-aminopyridines through intramolecular Co(I)-catalyzed [2+2+2] cycloaddition between ynamides, nitriles, and alkynes.

Authors:  Pierre Garcia; Solenne Moulin; Yves Miclo; David Leboeuf; Vincent Gandon; Corinne Aubert; Max Malacria
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

6.  Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes.

Authors:  Alexis Coste; François Couty; Gwilherm Evano
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

7.  Copper-catalyzed aerobic oxidative amidation of terminal alkynes: efficient synthesis of ynamides.

Authors:  Tetsuya Hamada; Xuan Ye; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

8.  Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides.

Authors:  Benoit Gourdet; Mairi E Rudkin; Ciorsdaidh A Watts; Hon Wai Lam
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  Application of ynamides in the synthesis of 2-amidoindoles.

Authors:  Karin Dooleweerdt; Thomas Ruhland; Troels Skrydstrup
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

10.  Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation.

Authors:  Ziyad F Al-Rashid; Richard P Hsung
Journal:  Org Lett       Date:  2008-01-17       Impact factor: 6.005
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  4 in total

1.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

2.  Copper-catalyzed Ficini [2 + 2] cycloaddition of ynamides.

Authors:  Hongyan Li; Richard P Hsung; Kyle A DeKorver; Yonggang Wei
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

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

Authors:  Renhe Liu; Gabrielle N Winston-McPherson; Zhong-Yue Yang; Xin Zhou; Wangze Song; Ilia A Guzei; Xiufang Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419

4.  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
  4 in total

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