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Synlett 2001; 2001(3): 0412-0414
DOI: 10.1055/s-2001-11400
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Chiral, Non-racemic, Distally-bridged Resorcin[4]arenes as Models for Use in Asymmetric Processes

Gareth Arnott* , Philip C. Bulman Page, Harry Heaney, Roger Hunter, Edward P. Sampler
  • *Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa; Fax + 27(21)6 89 74 99; E-mail: Roger@psipsy.uct.ac.za
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Publication History

Publication Date:
31 December 2001 (online)

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The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C11H23) is reported. The key step makes use of the Mannich reaction for attachment of a chiral diamine-line 2 across the cavity. Yields for this step are good to excellent. One of the bridged compounds exhibits modest activity (27% ee) as an enantioselective catalyst in the addition of diethylzinc to benzaldehyde.

bridged resorcin[4]arene - chiral resorcin[4]arene - Mannich reaction - enantioselective catalyst - C 2v -symmetric diamine chiral auxiliary

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