COMPETITIVE ORTHO-METALATION EFFECTS - THE KINETIC AND THERMODYNAMIC LITHIATION OF (TERT-BUTOXYCARBONYL)AMINO-4-CARBOMETHOXYTHIOPHENE

Authors
CARROLL WA ZHANG XL
Citation
Wa. Carroll et Xl. Zhang, COMPETITIVE ORTHO-METALATION EFFECTS - THE KINETIC AND THERMODYNAMIC LITHIATION OF (TERT-BUTOXYCARBONYL)AMINO-4-CARBOMETHOXYTHIOPHENE, Tetrahedron letters, 38(15), 1997, pp. 2637-2640
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
15
Year of publication
1997
Pages
2637 - 2640
Database
ISI
SICI code
0040-4039(1997)38:15<2637:COE-TK>2.0.ZU;2-M
Abstract
Deprotonation of the thiophene 1 under kinetically controlled conditio ns with LDA takes place next to the NHBoc group and under thermodynami c conditions next to the methyl ester. N-Methylation leads to exclusiv e lithiation next to the ester. The methyl ester was found to be super ior to the diethylamide in facilitating lithiation. (C) 1997 Elsevier Science Ltd.