Benzotriazole-assisted β-lithiation of vinyl ethers

DOI: 10.1016/S0040-4020(01)90453-3

Source and publish data:

Tetrahedron p. 6005 - 6016 (1994)

Update date:2022-08-18

Topics:

Authors:

Katritzky

Katritzky, Alan R.

Ignatchenko

Ignatchenko, Alexey V.

Lan Lan

Lan, Xiangfu

Lang Lang

Lang, Hengyuan

Stevens Stevens

Stevens, Christian V.

Opitz Opitz

Opitz, Andreas

Koch Koch

Koch, Rainer

Anders Anders

Anders, Ernst

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Article abstract of DOI:10.1016/S0040-4020(01)90453-3

Benzotriazole-assisted β-deprotonation of (α-benzotriazolylvinyl) ethers occurs stereoselectively at the cis position as shown by quenching with a variety of electrophiles. Semiempirical calculations of the lithiated enol ethers by PM3 and MNDO methods disclosed a higher stabilization for the cis-isomers over the corresponding trans-isomers

Full text of DOI:10.1016/S0040-4020(01)90453-3

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