Journal article
Electrophile‐Directed Diastereoselective Oxonitrile Alkylations
Chemistry : a European journal, v 24(12), pp 2850-2853
26 Feb 2018
PMID: 29327787
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Diastereoselective alkylation of prochiral oxonitrile dianions with secondary alkyl halides efficiently installs two contiguous stereogenic centers. The confluence of nucleophilic trajectory and the electrophile chirality causes distinct steric differences that allow efficient discrimination for one of the six possible conformers. Numerous oxonitrile‐derived dianions efficiently displace secondary alkyl halides propagating the electrophile chirality to efficiently install two contiguous tertiary centers. The prevalence of chiral, secondary electrophiles makes the interdigitated alkylation of chiral electrophiles a particularly attractive route because the resulting oxonitriles are readily transformed into bioactive heterocycles.
Two for one! Interdigital alkylations of oxonitrile dianions with secondary alkyl halides propagates the singular electrophile stereocenter into two new chiral centers. The confluence of nucleophilic trajectory and electrophile chirality favors one of six possible conformers to efficiently install two contiguous tertiary centers in oxonitriles that are readily transformed into bioactive heterocycles.
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Details
- Title
- Electrophile‐Directed Diastereoselective Oxonitrile Alkylations
- Creators
- Sergiy V. Chepyshev - Drexel UniversityBhaskar Reddy Pitta - Biophore India Hyderabad IndiaSaidi Reddy Vangala - Clearsynth Laboratories Hyderabad IndiaJ. Armando Lujan‐Montelongo - Centro de Investigación y de Estudios Avanzados (Cinvestav)Omar W. Steward - Duquesne UniversityFraser F. Fleming - Drexel University
- Publication Details
- Chemistry : a European journal, v 24(12), pp 2850-2853
- Publisher
- Wiley
- Number of pages
- 4
- Grant note
- Directorate for Mathematical and Physical Sciences (1464494)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000429415200009
- Scopus ID
- 2-s2.0-85041610438
- Other Identifier
- 991019169699704721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Multidisciplinary