Norbornanoid Chiral Ketones by Desymmetrization of Dibromoalkenes

New optically active polycyclic ketones 6a–6d, amenable to a large variety of synthetic applications, have been prepared from readily available 2,3‐dibromonorbornene and analogs (Scheme 2) via desymmetrization with (−)‐ephedrine, followed by hydrolysis under mild acidic conditions. At variance with...

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Bibliographic Details
Published in:Helvetica chimica acta 2014-04, Vol.97 (4), p.537-545
Main Authors: Koçak, Ramazan, Borsato, Giuseppe, De Lucchi, Ottorino, Daştan, Arif
Format: Article
Language:English
Subjects:
(−)-Ephedrine
Benzonorbornadiene
chiral
Desymmetrization
Enantioselectivity
Ketones
Ketones, chiral
Norbornanes
Norbornenones
Norbornenones, chiral
Oxazolidine
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Summary:New optically active polycyclic ketones 6a–6d, amenable to a large variety of synthetic applications, have been prepared from readily available 2,3‐dibromonorbornene and analogs (Scheme 2) via desymmetrization with (−)‐ephedrine, followed by hydrolysis under mild acidic conditions. At variance with substrates 4a–4d, the sterically hindered norbornene derivative 4e reacts with the solvent N‐methylpyrrolidin‐2‐one (NMP) leading to the formation of the unusual cyclopropanoid products 8a and 8b.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201300191