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Published August 24, 2005 | Supplemental Material
Journal Article Open

Enantioselective Organocatalytic Intramolecular Diels−Alder Reactions. The Asymmetric Synthesis of Solanapyrone D


The first direct enantioselective organocatalytic intramolecular Diels−Alder reaction has been accomplished. The use of iminium catalysis has provided a new catalytic strategy for the enantioselective [4 + 2] cycloisomerization of a wide variety of tethered diene-enal systems. The use of imidazolidinones 1 and 2 as the asymmetric catalysts has been found to mediate the enantioselective construction of [4.4.0] and [4.3.0] ring systems. Application of this methodology to the highly efficient asymmetric synthesis of the marine metabolite solanpyrone D has also been accomplished. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. Importantly, this technology has been utilized to execute the first enantioselective, catalytic Type II IMDA reaction.

Additional Information

© 2005 American Chemical Society. Received June 16, 2005. Publication Date (Web): July 28, 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen, Merck, and Astellas USA Foundation. W.S.J. and R.M.W. are grateful for NSF Predoctoral Fellowships.

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Supplemental Material - ja054008qsi20050720_022414.pdf


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