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DOI: 10.1055/s-0034-1381037
Diels–Alder Reactions of 1,3-Dienes Incorporated into 8-Oxa- and 8-Thiabicyclo[3.2.1]octane Skeletons: A Convenient Access to Complex Tri- and Tetracyclic Compounds
Publikationsverlauf
Received: 07. Mai 2015
Accepted after revision: 20. Mai 2015
Publikationsdatum:
24. Juni 2015 (online)
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Abstract
The Diels–Alder reactions of eight different 1,3-dienes incorporated into an 8-oxa- or 8-thiabicyclo[3.2.1]octane backbone were studied employing N-phenylmaleimide as standard dienophile. The facial diastereoselectivity was very high, in all cases furnishing only products resulting from a top-face attack. The [4+2] cycloadditions proceeded often with high exo/endo selectivity depending on the substitution degree of the 1,3-diene system. For one of the 1,3-dienes it could be demonstrated that the scope of the Diels–Alder reaction is fairly broad. The approach described here allows an efficient and fast access to complex tri- and tetracyclic compounds ready for further functionalization.
Key words
1,3-dienes - 8-oxabicyclo[3.2.1]octanes - cycloadditions - 1H-pyrrole-2,5-diones - stereoselectivity - regioselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1381037. Details of the MM2 calculations and copies of selected spectra are included.
- Supporting Information
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