Literature DB >> 10891170

Unusual Diastereoselectivity in Intramolecular Diels-Alder Reactions of Substituted 3,5-Hexadienyl Acrylates. Preference for a Boatlike Structure of the Six-Atom Tether Due to Ester Overlap.

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Abstract

Thermolysis of the 3,5-hexadienyl acrylates (a) proceeds via the transition state E in which the connecting chain adopts a boatlike conformation due to a preference for maintaining ester overlap to afford the products b with good diastereoselectivity.

Entities:  

Year:  2000        PMID： 10891170     DOI： 10.1021/ol000104e

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


  2 in total

1.  Ethyl (4aR*,7S*,8S*,8aS*)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexa-hydro-1H-isochromene-8-carboxyl-ate.

Authors:  Xiu Qing Jiang; Jin-Long Wu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-15

2.  Tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds.

Authors:  Javier Miró; María Sánchez-Roselló; Álvaro Sanz; Fernando Rabasa; Carlos Del Pozo; Santos Fustero
Journal:  Beilstein J Org Chem       Date:  2015-08-25       Impact factor: 2.883
  2 in total

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