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Synthesis 2005(16): 2701-2712  
DOI: 10.1055/s-2005-872108
PAPER
© Georg Thieme Verlag Stuttgart · New York

Lower Rim Functionalized Chiral Resorc[4]arenes Derived from Citronellal and Carvone

Michael Schiendorfer, Jochen Mattay*
Organische Chemie I, Fakultät für Chemie, Universität Bielefeld, Postfach 100131, 33501 Bielefeld, Germany
Fax: +49(0)5211066417; e-Mail: mattay@uni-bielefeld.de;
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Publication History

Received 14 February 2005
Publication Date:
04 August 2005 (online)

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Abstract

In our work we have provided the lower rim of resorc[4]arenes with stereogenic centers as well as with functional groups. For the synthesis of these lower rim functionalized chiral resorc[4]arenes we have used aldehydes derived from citronellal and carvone. In general, the functional group was introduced into the aldehyde compound prior to the final cyclization step. In the case of substitution of the functional group by chloride ions during the cyclization step under standard conditions (HCl-EtOH, Δ), hydrochloric acid was replaced by the conjugated acid of the functional group. Another strategy is the introduction of the iodo group at the lower rim of a resorc[4]arene, which can be easily substituted by good nucleophiles and mild bases without protection of the upper rim.

Key words

resorcarenes - macrocycles - chirality - molecular recognition - aldehydes - cyclizations

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Schiendorfer M., Mattay J. Acta Cryst. C, submitted.