Literature DB >> 20025256

Ligand-controlled enantioselective [2 + 2] cycloaddition of oxabicyclic alkenes with terminal alkynes using chiral iridium catalysts.

Bao-Min Fan1, Xiao-Jiao Li, Fang-Zhi Peng, Hong-Bin Zhang, Albert S C Chan, Zhi-Hui Shao.   

Abstract

The first catalytic asymmetric [2 + 2] cycloaddition of oxabicyclic alkenes and terminal alkynes has been developed. This iridium-catalyzed enantioselective [2 + 2] cycloaddition allows the formation of four stereocenters in a single step with excellent enantioselectivity (94-->99% ee).

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Year:  2010        PMID： 20025256     DOI： 10.1021/ol902574c

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


  7 in total

1.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

2.  Differential reactivities of enyne substrates in ruthenium- and palladium-catalyzed cycloisomerizations.

Authors:  Barry M Trost; Alicia C Gutierrez; Eric M Ferreira
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

3.  Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-01       Impact factor: 2.883

4.  Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture.

Authors:  M Elena de Orbe; Laura Amenós; Mariia S Kirillova; Yahui Wang; Verónica López-Carrillo; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

5.  Neutral chiral cyclopentadienyl Ru(ii)Cl catalysts enable enantioselective [2+2]-cycloadditions.

Authors:  D Kossler; N Cramer
Journal:  Chem Sci       Date:  2017-01-19       Impact factor: 9.825

6.  Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2] Cycloaddition with Non-C2 Symmetric Digold Catalysts.

Authors:  Cristina García-Morales; Beatrice Ranieri; Imma Escofet; Laura López-Suarez; Carla Obradors; Andrey I Konovalov; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2017-09-22       Impact factor: 15.419

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
  7 in total

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