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

doi:10.1016/S0040-4039(98)01930-3

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

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

46 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 language	English
Pages (from-to)	8377-8380
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(98)01930-3
Publication status	Published - 12 Nov 1998

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10.1016/S0040-4039(98)01930-3

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

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.",

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T2 - Deuterium as a protecting group for carbon

AU - Clayden, Jonathan

AU - Pink, Jennifer H.

AU - Westlund, Neil

AU - Wilson, Francis X.

PY - 1998/11/12

Y1 - 1998/11/12

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4039(98)01930-3

DO - 10.1016/S0040-4039(98)01930-3

M3 - Article (Academic Journal)

AN - SCOPUS:0032511947

VL - 39

SP - 8377

EP - 8380

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -

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

Abstract

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