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- Title
Enantioselective Installation of Quaternary Centers in Cyclic Oxonitriles.
- Authors
Gunes, Yakup; Arcelik, Nejat; Sahin, Ertan; Fleming, Fraser F.; Altundas, Ramazan
- Abstract
Quaternary centers are rapidly and selectively installed in a series of seven-membered and bridged cyclic oxonitriles through conjugate addition of an alkoxide to chloroalkenenitriles, followed by a Claisen rearrangement. Using this strategy, the stereogenic information of the carbinol in secondary allylic alcohols is transferred to the newly generated quaternary center. Experimentally, the sequence rapidly gives alkyl cyanocycloheptanones and bicycloalkanonecarbonitriles in good yield and with high selectivity, in a single synthetic operation.
- Subjects
NITRILE synthesis; OXO compounds; ENANTIOSELECTIVE catalysis; CHLOROALKANES; ALKOXIDES; HEPTANONES; CLAISEN rearrangement
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 30, p6679
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500895