Controlling the regioselectivity of lithiation using kinetic isotope effects: Deuterium as a protecting group for carbon

Jonathan Clayden*, Jennifer H. Pink, Neil Westlund, Francis X. Wilson

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

43 Citations (Scopus)

Abstract

By substituting deuterium for hydrogen at positions of high kinetic acidity in amides and carbamates, the usual regiochemical course of their reactions with alkyllithiums (ortholithiation vs. lateral lithiation vs. nucleophilic addition) can be altered or overturned by the kinetic isotope effect. The deuterium substituent functions in these reactions as a protecting group for carbon.

Original languageEnglish
Pages (from-to)8377-8380
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number46
DOIs
Publication statusPublished - 12 Nov 1998

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