Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8‐Dipropyltetrathia[7]helicenes | Zendy

Doulcet Julien | Zendy; Stephenson G. Richard | Zendy

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Novel Asymmetric Formylation of Aromatic Compounds: Enantioselective Synthesis of Formyl 7,8‐Dipropyltetrathia[7]helicenes

Author(s) -

Doulcet Julien,

Stephenson G. Richard

Publication year - 2015

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201501627

Subject(s) - enantioselective synthesis , formylation , chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis

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 = i Pr, R 2 =Me, R 3 =H, R 4 =1‐naphthyl or its 1‐pyrenyl equivalent.

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