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Journal article
Metalated Nitriles: Internal 1,3-Asymmetric Induction
European journal of organic chemistry, v 2009(5), pp 699-708
Feb 2009
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Abstract
Stereoselective alkylations of acyclic, metalated nitriles are intimately controlled by a remote stereocenter. Probing the optimal steric demand through alkylations with a series of substituted pentanenitriles reveal the fundamental requirements for 1,3-asymmetric induction. Relaying these requirements into a predictive model suggests that the stereoselectivity arises from a preferential electrophilic attack on the more stable diamond lattice conformation of the metalated nitrile. Using this strategy a series of metalated alkanenitriles selectively intercept a diverse range of electrophiles in alkylations that efficiently install new quaternary centers. The metalated nitrile alkylations provide fundamental insight for remote stereoinduction and a solid foundation for further advances in stereoselective alkylations of flexible nucleophiles having a defined shape. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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Details
- Title
- Metalated Nitriles: Internal 1,3-Asymmetric Induction
- Creators
- Fraser F. Fleming - Duquesne UniversityWang Liu - Duquesne University
- Publication Details
- European journal of organic chemistry, v 2009(5), pp 699-708
- Publisher
- Wiley
- Number of pages
- 10
- Grant note
- CHE 0515715; CRIF 024872; CHE 0421252; CHE 0614785 / National Science Foundation (NSF)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000263512300011
- Scopus ID
- 2-s2.0-60849101828
- Other Identifier
- 991020898498904721
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- Web of Science research areas
- Chemistry, Organic