Literature DB >> 16316211

Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones.

Reema K Thalji1, William R Roush.   

Abstract

We report a phosphine-mediated intramolecular aldol cyclization of unsaturated diketones that proceeds with extremely high levels of regioselectivity for the cross-conjugated bicyclic dienone products. The sense of regioselectivity observed in this reaction is complementary to that obtained using traditional aldol conditions. Experimental evidence that supports the involvement of a phosphine Michael adduct is described.

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Year:  2005        PMID： 16316211      PMCID： PMC2515627          DOI： 10.1021/ja054085l

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


  9 in total

1.  New Strategies for the Development of an Asymmetric Version of the Baylis-Hillman Reaction This work was supported by the Fonds der Chemischen Industrie (Liebig-scholarship and funds for P. L.). P. L. thanks Prof. Dr. A. de Meijere for his support.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

2.  Synthetic studies toward FR182877. Remarkable solvent effect in the vinylogous morita-baylis-hillman cyclization.

Authors:  Joey L Methot; William R Roush
Journal:  Org Lett       Date:  2003-10-30       Impact factor: 6.005

3.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

4.  Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn A tricyclic nucleus.

Authors:  Dustin J Mergott; Scott A Frank; William R Roush
Journal:  Org Lett       Date:  2002-09-05       Impact factor: 6.005

5.  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

6.  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

7.  Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A.

Authors:  Kyriacos Agapiou; Michael J Krische
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

8.  Phosphine-catalyzed hydration and hydroalkoxylation of activated olefins: use of a strong nucleophile to generate a strong base.

Authors:  Ian C Stewart; Robert G Bergman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2003-07-23       Impact factor: 15.419

9.  Phosphine-mediated [4 + 2] annulation of bis(enones): a Lewis base catalyzed "mock Diels-Alder" reaction.

Authors:  Michel Couturier; Fréderic Ménard; John A Ragan; Maxime Riou; Etienne Dauphin; Brian M Andresen; Arun Ghosh; Kristina Dupont-Gaudet; Mélina Girardin
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
  9 in total
  8 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.  N-Heterocyclic Carbene-Promoted Rauhut]Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes.

Authors:  Roxanne L Atienza; Karl A Scheidt
Journal:  Aust J Chem       Date:  2011-08-19       Impact factor: 1.321

4.  Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.

Authors:  Vardhineedi Sriramurthy; Ohyun Kwon
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

5.  Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.

Authors:  Kui Zhang; Lingchao Cai; Sooji Hong; Ohyun Kwon
Journal:  Org Lett       Date:  2019-06-20       Impact factor: 6.005

6.  Synthesis of 7-epineoptilocaulin, mirabilin B, and isoptilocaulin. A unified biosynthetic proposal for the ptilocaulin and batzelladine alkaloids. Synthesis and structure revision of netamines E and G.

Authors:  Min Yu; Susan S Pochapsky; Barry B Snider
Journal:  J Org Chem       Date:  2008-10-18       Impact factor: 4.354

7.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

8.  The roles of counterion and water in a stereoselective cysteine-catalyzed Rauhut-Currier reaction: a challenge for computational chemistry.

Authors:  Sílvia Osuna; Alpay Dermenci; Scott J Miller; K N Houk
Journal:  Chemistry       Date:  2013-09-03       Impact factor: 5.236
  8 in total

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