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On the use of deuterium isotope effects in chemical synthesis

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
32
Identifiers
DOI: 10.1016/s0040-4039(02)01114-0

Abstract

Abstract The decreased kinetic acidity of deuterium relative to hydrogen can be used to gain an advantage in the reductive cyclization of an alkenyllithium species onto a ketone. The intermediate alkenyllithium can add to the carbonyl or abstract an α-proton, giving rise to two products. The yield of the cyclized product can be increased, and the formation of the uncyclized by-product can be suppressed, by replacing the acidic protons with deuterons prior to cyclization.

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