Spiro Tröger's base derivatives: another structural phoenix?

Ameneh Tatar; Jan Cejka; Vladimír Král; Bohumil Dolenský

doi:10.1021/ol1004774

Spiro Tröger's base derivatives: another structural phoenix?

Org Lett. 2010 Apr 16;12(8):1872-5. doi: 10.1021/ol1004774.

Authors

Ameneh Tatar¹, Jan Cejka, Vladimír Král, Bohumil Dolenský

Affiliation

¹ Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technicka 5, Praha 166 28, Czech Republic.

PMID: 20334388
DOI: 10.1021/ol1004774

Abstract

Recently, naphthalenoide derivatives of Troger's base (TB) have become important as structural compartments of molecular tweezers and compounds with high specific rotation. The formation of TB derivatives and byproducts from naphthalen-2-amine, methyl 6-aminonaphthalene-2-carboxylate, and anthracen-2-amine was studied. It was discovered that the formation of a naphthalenoide TB derivative is followed by the formation of a unique structural isomer of TB: spiroTB.