Journal article
Enantioselective Installation of Quaternary Centers in Cyclic Oxonitriles
European journal of organic chemistry, v 2015(30), pp 6679-6686
Oct 2015
Featured in Collection : UN Sustainable Development Goals @ Drexel
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.
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Details
- Title
- Enantioselective Installation of Quaternary Centers in Cyclic Oxonitriles
- Creators
- Yakup Gunes - Atatürk UniversityNejat Arcelik - Atatürk UniversityErtan Sahin - Atatürk UniversityFraser F. Fleming - Duquesne UniversityRamazan Altundas - Atatürk University
- Publication Details
- European journal of organic chemistry, v 2015(30), pp 6679-6686
- Publisher
- Wiley
- Number of pages
- 8
- Grant note
- BAP-2009-244-B / Ataturk University
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000363339600013
- Scopus ID
- 2-s2.0-84945481359
- Other Identifier
- 991020898396104721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic