Synthesis 2015; 47(18): 2767-2775
DOI: 10.1055/s-0034-1381037
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Jens Högermeier
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
,
Daniel Trawny
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
,
Reinhold Zimmer
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
,
Hans-Ulrich Reissig*
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
› Author Affiliations
Further Information

Publication History

Received: 07 May 2015

Accepted after revision: 20 May 2015

Publication Date:
24 June 2015 (online)

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.

Supporting Information

 
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