Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 38, Pages 13431-13436Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501627
Keywords
asymmetric synthesis; chiral formamides; double-kinetic resolution; enantioselective formylation; kinetic resolution
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Funding
- EPSRC [EH/C009922]
- EU [4196]
- EPSRC [EP/H009922/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H009922/1] Funding Source: researchfish
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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 R-1=iPr, R-2=Me, R-3=H, R-4=1-naphthyl or its 1-pyrenyl equivalent.
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