Literature DB >> 15053596

Phosphine-mediated reductive condensation of gamma-acyloxy butynoates: a diversity oriented strategy for the construction of substituted furans.

Cheol-Kyu Jung1, Jian-Cheng Wang, Michael J Krische.   

Abstract

Exposure of gamma-acyloxy butynoates to stoichiometric quantities of triphenylphosphine results in reductive condensation to afford substituted furans, by way of allenic ester intermediates. As gamma-acyloxy butynoates are readily obtained through condensation of ethyl propiolate with aldehydes followed by acylation, this method represents a powerful and mechanistically novel protocol for the convergent three-component construction of substituted furans.

Entities:  

Year:  2004        PMID： 15053596     DOI： 10.1021/ja049377l

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


  9 in total

1.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

Review 2.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

3.  An expedient route to substituted furans via olefin cross-metathesis.

Authors:  Timothy J Donohoe; John F Bower
Journal:  Proc Natl Acad Sci U S A       Date:  2010-02-08       Impact factor: 11.205

4.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

5.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

6.  Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates.

Authors:  Gardner S Creech; Ohyun Kwon
Journal:  Org Lett       Date:  2008-01-04       Impact factor: 6.005

7.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

8.  Synthesis of 2-Alkynoates by Palladium(II)-Catalyzed Oxidative Carbonylation of Terminal Alkynes and Alcohols.

Authors:  Qun Cao; N Louise Hughes; Mark J Muldoon
Journal:  Chemistry       Date:  2016-07-19       Impact factor: 5.236

9.  Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.

Authors:  Kui Zhang; Lingchao Cai; Zhongyue Yang; K N Houk; Ohyun Kwon
Journal:  Chem Sci       Date:  2018-01-18       Impact factor: 9.825
  9 in total

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