Premium
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.