Literature DB >> 21526771

Ruthenium-catalyzed (2 + 2) intramolecular cycloaddition of allenenes.

Moisés Gulías1, Alba Collado, Beatriz Trillo, Fernando López, Enrique Oñate, Miguel A Esteruelas, José L Mascareñas.   

Abstract

We report a ruthenium-catalyzed (2 + 2) intramolecular cycloaddition of allenes and alkenes. We have found that the use of the ruthenium complex RuH(2)Cl(2)(P(i)Pr(3))(2), which has previously gone unnoticed in catalytic applications, is crucial for the observed reactivity. The reaction proceeds under mild conditions and is fully diastereoselective, providing a practical entry to a variety of bicyclo[3.2.0]heptane skeletons featuring cyclobutane rings.

Entities:  

Year:  2011        PMID： 21526771     DOI： 10.1021/ja200784n

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


  8 in total

1.  Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.

Authors:  Yao Xu; Young J Hong; Dean J Tantillo; M Kevin Brown
Journal:  Org Lett       Date:  2017-07-07       Impact factor: 6.005

2.  Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

Authors:  Chao Ning; Kang-Hua Rui; Yin Wei; Min Shi
Journal:  Chem Sci       Date:  2022-06-01       Impact factor: 9.969

3.  Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.

Authors:  Nathan J Line; Brittany P Witherspoon; Erin N Hancock; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-10-06       Impact factor: 15.419

4.  Gold(I)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: efficient access to highly substituted cyclobutanes.

Authors:  Paloma Bernal-Albert; Hélio Faustino; Ana Gimeno; Gregorio Asensio; José L Mascareñas; Fernando López
Journal:  Org Lett       Date:  2014-11-19       Impact factor: 6.005

5.  Cobalt-Catalyzed [2π + 2π] Cycloadditions of Alkenes: Scope, Mechanism, and Elucidation of Electronic Structure of Catalytic Intermediates.

Authors:  Valerie A Schmidt; Jordan M Hoyt; Grant W Margulieux; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

6.  A rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles.

Authors:  Yirong Zhou; Ali Nikbakht; Felix Bauer; Bernhard Breit
Journal:  Chem Sci       Date:  2019-04-03       Impact factor: 9.825

7.  Ruthenium-Catalyzed [2 + 2] versus Homo Diels-Alder [2 + 2 + 2] Cycloadditions of Norbornadiene and Disubstituted Alkynes: A DFT Study.

Authors:  Austin Pounder; Leanne D Chen; William Tam
Journal:  ACS Omega       Date:  2020-12-18

8.  Tandem Ring Opening/Intramolecular [2 + 2] Cycloaddition Reaction for the Synthesis of Cyclobutane Fused Thiazolino-2-Pyridones.

Authors:  Mohit Tyagi; Dan E Adolfsson; Pardeep Singh; Jörgen Ådén; Sanduni Wasana Jayaweera; Anna Gharibyan; Jaideep B Bharate; Anita Kiss; Souvik Sarkar; Anders Olofsson; Fredrik Almqvist
Journal:  J Org Chem       Date:  2021-11-12       Impact factor: 4.354
  8 in total

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