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Whisler MC, MacNeil S, Snieckus V, et al. Beyond thermodynamic acidity: a perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions. Angew Chem Int Ed Engl. 2004;43(17):2206-25doi: 10.1002/anie.200300590.
Whisler, M. C., MacNeil, S., Snieckus, V., & Beak, P. (2004). Beyond thermodynamic acidity: a perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions. Angewandte Chemie (International ed. in English), 43(17), 2206-25. https://doi.org/10.1002/anie.200300590
Whisler, Marna C, et al. "Beyond thermodynamic acidity: a perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions." Angewandte Chemie (International ed. in English) vol. 43,17 (2004): 2206-25. doi: https://doi.org/10.1002/anie.200300590
Whisler MC, MacNeil S, Snieckus V, Beak P. Beyond thermodynamic acidity: a perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions. Angew Chem Int Ed Engl. 2004 Apr 19;43(17):2206-25. doi: 10.1002/anie.200300590. PMID: 15108128.
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Angew Chem Int Ed Engl. 2004 Apr 19;43(17):2206-25. doi: 10.1002/anie.200300590.

Beyond thermodynamic acidity: a perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions.

Angewandte Chemie (International ed. in English)

Marna C Whisler, Stephen MacNeil, Victor Snieckus, Peter Beak

Affiliations

  1. Johnson and Johnson, Pharmaceutical Research and Development, L.L.C., La Jolla, CA, USA.

PMID: 15108128 DOI: 10.1002/anie.200300590

Abstract

The concept of the complex-induced proximity effect (CIPE) in deprotonations is helpful in elucidating the mechanisms involved in carbanion chemistry and in planning organic syntheses. In this Review, the consequences of complexation of organolithium bases to functional groups of the substrates before the proton-transfer step are discussed. Experimental data from kinetic measurements and isotope-labeling experiments as well as the results of calculations in many cases point to a prelithiation complex as a reaction intermediate. Some examples from natural products synthesis illustrate how this concept can be used to obtain intermediates in a regio- or stereoselective manner. Of particular interest is the functionalization of positions that are remote from the coordination group.

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