Jump to main content
Jump to site search

Issue 15, 2017
Previous Article Next Article

Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene

Author affiliations

Abstract

α,β-Unsaturated acylammonium salts are useful dienophiles enabling highly enantioselective and stereodivergent Diels-Alder-initiated organocascades with furan-based dienes. Complex polycyclic systems can thus be obtained from readily prepared dienes, commodity acid chlorides, and a chiral isothiourea organocatalyst under mild conditions. We describe the use of furan-based dienes bearing pendant sulfonamides leading to the generation of oxa-bridged, trans-fused tricyclic γ-lactams. This process constitutes the first highly enantio- and diastereoselective, organocatalytic Diels-Alder cycloadditions with these typically problematic dienes due to their reversibility. Computational studies suggest that the high diastereoselectivity with these furan dienes may be due to a reversible Diels-Alder cycloaddition for the endo adducts. In addition, the utility of this methodology is demonstrated through a concise approach to a core structure with similarity to the natural product isatisine A and a nonpeptidyl ghrelin-receptor inverse agonist.

Graphical abstract: Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Dec 2016, accepted on 10 Mar 2017 and first published on 15 Mar 2017


Article type: Communication
DOI: 10.1039/C6OB02738E
Citation: Org. Biomol. Chem., 2017,15, 3179-3183
  •   Request permissions

    Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene

    M. E. Abbasov, B. M. Hudson, W. Kong, D. J. Tantillo and D. Romo, Org. Biomol. Chem., 2017, 15, 3179
    DOI: 10.1039/C6OB02738E

Search articles by author

Spotlight

Advertisements