Intramolecular Carbolithiation of Heterosubstituted Alkynes: An Experimental and Theoretical Study

Rudy Lhermet, Maha Ahmad, Clémence Hauduc, Catherine Fressigné, Muriel Durandetti, Jacques Maddaluno

Chemistry - A European Journal · 2015 · 23 citations · 50 references

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Abstract

A series of heterosubstitued alkynes was successfully submitted to the intramolecular carbolithiation of their triple bond. We show that the addition is stereoselective because of the control exerted by the terminal substituent X on the geometry of the transition state. A complementary DFT study suggests that the addition is anti when a strong Li-X interaction occurs.

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