Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes

Doulcet, Julien and Stephenson, G. Richard (2015) Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes. Chemistry - A European Journal, 21 (38). 13431–13436. ISSN 0947-6539

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Abstract

Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8-dipropyltetrathia[7]helicene, affording the corresponding formyl- or diformylhelicenes in up to 73% ee, making enantiopure compounds available by recrystallisation. With the N,N-disubstituted formamides used in this study, the best enantioselectivity has been achieved with R1=iPr, R2=Me, R3=H, R4=1-naphthyl or its 1-pyrenyl equivalent.

Item Type: Article
Uncontrolled Keywords: asymmetric synthesis,chiral formamides,double kinetic resolution,enantioselective formylation,kinetic resolution,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1605
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 23 Jun 2016 09:00
Last Modified: 11 Nov 2020 00:46
URI: https://ueaeprints.uea.ac.uk/id/eprint/59472
DOI: 10.1002/chem.201501627

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