o-Selective metalation and electrophilic substitution of benzylamine derivatives

N-Pivaloylbenzylamines and derivs. [e.g., 2,4-R(MeO)C6H4CH2NHCOCMe3, I, R = H] undergo smooth ortho-metalation when treated with two equivs. of an organolithium reagent. Subsequent carboxylation or hydroxylation lead to a no. of products, e.g., I, R = CO2H, OH. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 29, 34, 4277-80
Year:
1988
Keywords:
Note:
CAN 110:192369
25-17
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
26209-45-0; 120226-41-7 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation and carboxylation of, regiochem. of); 60050-53-5P; 120226-39-3P; 120226-40-6P; 120226-43-9P; 120226-44-0P; 120226-45-1P; 120226-46-2P; 120226-47-3P; 120226-48-4P; 120226-51-9P; 120226-52-0P; 120226-53-1P; 120226-54-2P; 120226-56-4P; 120226-57-5P; 120226-58-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 120226-42-8; 120226-49-5; 120226-50-8; 120226-55-3 Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective metalation, carboxylation and borylation of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)