Journal article
Enantioselective Synthesis of Cyclic, Quaternary Oxonitriles
Journal of organic chemistry, v 75(21), pp 7092-7098
05 Nov 2010
PMID: 20936807
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively forming a new quaternary center with enantiomeric ratios typically greater than 9:I. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while simultaneously installing ketone, nitrite, and olefin functionalities.
Metrics
Details
- Title
- Enantioselective Synthesis of Cyclic, Quaternary Oxonitriles
- Creators
- Yakup Gunes - Atatürk UniversityM. Fatih Polat - Atatürk UniversityErtan Sahin - Atatürk UniversityFraser F. Fleming - Duquesne UniversityRamazan Altundas - Atatürk University
- Publication Details
- Journal of organic chemistry, v 75(21), pp 7092-7098
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 7
- Grant note
- BAP-2005-230 / Ataturk University 106T100 / TUBITAK; Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000283531100006
- Scopus ID
- 2-s2.0-78049505290
- Other Identifier
- 991020898500504721
UN Sustainable Development Goals (SDGs)
This publication has contributed to the advancement of the following goals:
InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic