TY - JOUR
T1 - Tröger's Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether
AU - Artacho Ruiz, Josep
AU - Ascic, Erhad
AU - Rantanen, Toni
AU - Wallentin, Carl-Johan
AU - Dawaigher, Sami
AU - Bergquist, Karl-Erik
AU - Harmata, Michael
AU - Snieckus, Victor
AU - Wärnmark, Kenneth
PY - 2012
Y1 - 2012
N2 - Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.
AB - Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.
U2 - 10.1021/ol302022y
DO - 10.1021/ol302022y
M3 - Article
C2 - 22958089
SN - 1523-7052
VL - 14
SP - 4706
EP - 4709
JO - Organic Letters
JF - Organic Letters
IS - 18
ER -