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Synthesis of Unsymmetrical Tröger's Bases Bearing Groups Sensitive to Reduction
Author(s) -
Havlík Martin,
Dolenský Bohumil,
Jakubek Milan,
Král Vladimír
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301517
Subject(s) - chemistry , trifluoroacetic acid , paraformaldehyde , alkylation , base (topology) , diamine , carbamate , aryl , medicinal chemistry , derivative (finance) , organic base , organic chemistry , combinatorial chemistry , catalysis , alkyl , mathematical analysis , mathematics , financial economics , economics
An efficient approach for the synthesis of unsymmetrically substituted Tröger's base derivatives is reported. This approach is based on the N ‐alkylation of an arylamine by tert ‐butyl [2‐(bromomethyl)aryl]carbamate to give the corresponding diamine, which is subsequently converted into a Tröger's base derivative using paraformaldehyde in trifluoroacetic acid. The mild conditions of this approach allow the preparation of Tröger's base derivatives bearing electron‐withdrawing functional groups sensitive to reducing conditions, as demonstrated by the preparation of twelve Tröger's base derivatives in overall yields of 62 to 76 %.