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Benzannulated Cycloheptanones from Binaphthyl Platforms
Author(s) -
Pieters Grégory,
Sbargoud Kamal,
Bridoux Alexandre,
Gaucher Anne,
Marque Sylvain,
Bourdreux Flavien,
Marrot Jérôme,
Flot David,
Wantz Guillaume,
Dautel Olivier,
Prim Damien
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201370
Subject(s) - electrophile , chemistry , intramolecular force , reagent , electrophilic substitution , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , catalysis
Preparations of benzannulated cycloheptanones starting from unique binaphthyl molecular platforms are described. Binaphthyl acetic acids proved suitable percursors for fused cycloheptanone architectures. Seven‐membered rings embedded in binaphthyl units were selectively generated by use of Eaton's reagent. Isomeric helical architectures arising from electrophilic cyclisation processes at second reaction sites in the precursors could also be obtained under different acidic conditions. Unambiguous discrimination between isomeric geometries was provided by multiple quantum NMR sequences. DFT calculations were performed and gave evidence of different behaviour of the substrates towards intramolecular electrophilic substitution. The theoretical approach confirmed the experimental results, agreeing completely with X‐ray data.