Literature DB >> 27232451

Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.

Qing-Fa Zhou1,2, Kui Zhang2, Lingchao Cai2, Ohyun Kwon2.   

Abstract

A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic esters is reported. This process appears to be practical for the stereoselective syntheses of (Z)-furan-2(3H)-one oxime derivatives in excellent yields. Mechanistically, the reaction involves a phosphine-catalyzed Michael addition of an alkylideneazinate and rearrangement of the cyclic nitronate to the α-nitrosodihydrofuran.

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Year:  2016        PMID： 27232451      PMCID： PMC4922534          DOI： 10.1021/acs.orglett.6b01299

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  45 in total

1.  Tandem reactions to construct heterocycles via phosphine-catalyzed umpolung addition and intramolecular conjugate addition.

Authors:  Cheng Lu; Xiyan Lu
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

2.  Synthesis of Highly Functionalized gamma-Butyrolactones from Activated Carbonyl Compounds and Dimethyl Acetylenedicarboxylate.

Authors:  Kyoko Nozaki; Naomasa Sato; Kazuhiro Ikeda; Hidemasa Takaya
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

3.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis.

Authors:  X Lu; C Zhang; Z Xu
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

4.  Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes.

Authors:  Xue-Feng Zhu; Christopher E Henry; Jay Wang; Travis Dudding; Ohyun Kwon
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

5.  Synthesis of (+)-casuarine.

Authors:  S E Denmark; A R Hurd
Journal:  J Org Chem       Date:  2000-05-19       Impact factor: 4.354

6.  Phosphine-catalyzed synthesis of 6-substituted 2-pyrones: manifestation of E/Z-isomerism in the zwitterionic intermediate.

Authors:  Xue-Feng Zhu; Arnaud-Pierre Schaffner; Ronald C Li; Ohyun Kwon
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

7.  Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.

Authors:  Long-Cheng Wang; Ana Liza Luis; Kyriacos Agapiou; Hye-Young Jang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

8.  The vinylogous intramolecular Morita-Baylis-Hillman reaction: synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts.

Authors:  Scott A Frank; Dustin J Mergott; William R Roush
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

9.  Phosphine-catalyzed annulation of thioamides and 2-alkynoates: a new synthesis of thiazolines.

Authors:  Bing Liu; Roman Davis; Biren Joshi; Daniel W Reynolds
Journal:  J Org Chem       Date:  2002-06-28       Impact factor: 4.354

10.  An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

Authors:  Xue-Feng Zhu; Jie Lan; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419
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  1 in total

Review 1.  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
  1 in total

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