Site selective substitution of carbamate and carbamoyl protected benzylamines

Methoxy- and fluoro-substituted benzylamines can be metalated optionally at the position adjacent to the nitrogen bearing side chain or adjacent to the hetero substituent as a function of the acyl-type protective group. Thus, lithiation of 2-FC6H4CH2NHBOC with BuLi/KOCMe3 in THF followed by carboxylation with CO2 and acid workup afforded 50% 2,3-F(HO2C)C6H3CH2NHBOC, whereas lithiation of 2-FC6H4CH2NHCONMe2 with LiCMe3 in THF followed by carboxylation afforded 81% 2,6-F(HO2C)C6H3CH2NHCONMe2 regioselectively. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 34, 39, 6263-4
Year:
1993
Keywords:
Note:
CAN 120:216883
25-21
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
153903-28-7; 153903-29-8 (N-(Tert-butoxycarbonyl)-3-fluorobenzylamine) Role: RCT (Reactant), RACT (Reactant or reagent) (attempted regioselective lithiation-carboxylation of); 3601-66-9P; 138350-86-4P; 153903-09-4P; 153903-10-7P; 153903-11-8P; 153903-12-9P; 153903-13-0P; 153903-14-1P; 153903-15-2P; 153903-16-3P; 153903-17-4P; 153903-18-5P; 153903-19-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 138350-83-1 Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective lithiation and subsequent reaction with DMF and acid); 35376-72-8; 42116-44-9 (N-(Tert-butoxycarbonyl)benzylamine); 64407-60-9; 120157-94-0; 153903-20-9; 153903-21-0; 153903-22-1; 153903-23-2; 153903-24-3; 153903-25-4; 153903-26-5; 153903-27-6 Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective lithiation-carboxylation of)
Laboratories:




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


Rate this document:

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