Literature DB >> 26351987

B(C6F5)3: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals.

Jia-Hui Zhou1, Bing Jiang1, Fei-Fan Meng1, Yun-He Xu1, Teck-Peng Loh1,2.   

Abstract

Lewis acid B(C6F5)3 catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the product's stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.

Entities:  

Year:  2015        PMID: 26351987     DOI: 10.1021/acs.orglett.5b02066

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


  4 in total

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Authors:  Jeffrey Buter; Dorus Heijnen; Ieng Chim Wan; F Matthias Bickelhaupt; David C Young; Edwin Otten; D Branch Moody; Adriaan J Minnaard
Journal:  J Org Chem       Date:  2016-07-26       Impact factor: 4.354

2.  Origin of Catalysis and Selectivity in Lewis Acid-Promoted Diels-Alder Reactions Involving Vinylazaarenes as Dienophiles.

Authors:  Susana Portela; Israel Fernández
Journal:  J Org Chem       Date:  2022-07-06       Impact factor: 4.198

3.  Total synthesis of nahuoic acid A via a putative biogenetic intramolecular Diels-Alder (IMDA) reaction.

Authors:  Lucía Guillade; Paula Mora; Pedro Villar; Rosana Alvarez; Angel R de Lera
Journal:  Chem Sci       Date:  2021-10-27       Impact factor: 9.825

4.  Enantioselective Total Synthesis of (+)-Heilonine.

Authors:  Kyle J Cassaidy; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2021-09-29       Impact factor: 15.419

  4 in total

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