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

Doulcet, Julien and Stephenson, G. Richard ORCID: https://orcid.org/0000-0003-1487-9178 (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

Microsoft Word (Stepehnson-Doulcet_DOI_10.1002_chem.201501627) - Accepted Version Download (1MB)

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
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Pure Connector
Date Deposited:	23 Jun 2016 09:00
Last Modified:	21 Oct 2022 01:17
URI:	https://ueaeprints.uea.ac.uk/id/eprint/59472
DOI:	10.1002/chem.201501627

Downloads

Actions (login required)

View Item