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Intramolecular Carbolithiation of Heterosubstituted Alkynes: An Experimental and Theoretical Study |
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| Authors: | Dr. Rudy Lhermet Maha Ahmad Clémence Hauduc Dr. Catherine Fressigné Dr. Muriel Durandetti Dr. Jacques Maddaluno |
| Affiliation: | Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France) |
| 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. |
| Keywords: | alkynes carbenoids cyclization density functional calculations lithiation |