Novel Asymmetric Formylation of Aromatic Compounds

Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes

Julien Doulcet, G. Richard Stephenson

Research output: Contribution to journalArticle

15 Citations (Scopus)

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. Why have chiral formamides been overlooked for so long as tools in asymmetric synthesis? Herein new and efficient procedures are described in which enantioselective delivery of the formyl group achieves kinetic resolution and double kinetic resolution of helicenes, a class of chiral fused aromatic structures that are notoriously difficult to prepare in enantiopure form.

Original languageEnglish
Pages (from-to)13431-13436
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number38
DOIs
Publication statusPublished - 14 Sep 2015
Externally publishedYes

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Formamides
Aromatic compounds
Kinetics
Enantioselectivity
helicenes

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Novel Asymmetric Formylation of Aromatic Compounds : Enantioselective Synthesis of Formyl 7,8-Dipropyltetrathia[7]helicenes. / Doulcet, Julien; Stephenson, G. Richard.

In: Chemistry - A European Journal, Vol. 21, No. 38, 14.09.2015, p. 13431-13436.

Research output: Contribution to journalArticle

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