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 (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Rachel Smith
Date Deposited:	21 Jun 2011 11:39
Last Modified:	24 Sep 2024 10:21
URI:	https://ueaeprints.uea.ac.uk/id/eprint/32820
DOI:	10.1055/s-2001-11400

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