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Issue 15, 2017
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Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene

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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

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Article information


Submitted
14 Dec 2016
Accepted
10 Mar 2017
First published
15 Mar 2017

Org. Biomol. Chem., 2017,15, 3179-3183
Article type
Communication

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

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