Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes

Arnott, Gareth, Bulman Page, Philip C., Heaney, Harry, Hunter, Roger and Sampler, Edward P. (2001) Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes. Synlett, 3. pp. 412-414. ISSN 0936-5214

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Abstract

The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 with various R groups (CH3, C5H11, C-11 H-23) 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.

Item Type: Article
Uncontrolled Keywords: bridged resorcin[4]arene,acid,alkylation,chiral resorcin[4]arene.,calixarenes,mannich reaction,resorcarenes,enantioselective catalyst,ring,c-2v-symmetric diamine chiral auxiliary,calix<4>resorcinarene derivatives,selective derivatization,closure,resorcinol,aldehydes
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 12:39
Last Modified: 17 Apr 2019 10:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/32820
DOI: 10.1055/s-2001-11400

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