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Synfacts 2008(2): 0205-0205  
DOI: 10.1055/s-2007-992431
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

A Calix[4]pyrrole Organocatalyst

Contributor(s): Benjamin List, Subhas Chandra Pan
G. Cafeo, M. De Rosa, F. H. Kohnke*, P. Neri, A. Soriente*, L. Valenti
Universitá di Messina and Universitá di Salerno, Italy
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The authors introduce calix[4]pyrrole 1 as a new catalyst motif for the hetero-Diels-Alder reaction of Danishefsky’s diene and 4-nitro­benzaldehyde. Using two equivalents of the aldehyde, the authors obtained a mixture of products 2 and 3. At high concentration ketone 2 is the major product and at low concentration aldol 3 is the major product. Diels-Alder adduct 4 was obtained when five equivalents of the aldehyde were used.