TY - JOUR
T1 - Unexpected isocyanide-based three-component bicyclization for the
stereoselective synthesis of densely functionalized
pyrano[3,4-c]pyrroles
AU - Gao, Qian
AU - Hao, Wen-Juan
AU - Liu, Feng
AU - Tu, Shu-Jiang
AU - Wang, Shu-Liang
AU - Li, Guigen
AU - Jiang, Bo
PY - 2016
Y1 - 2016
N2 - A novel three-component bicyclization strategy for the efficient
synthesis of densely functionalized pyrano[3,4-c]pyrroles has been
established from readily accessible 3-aroylacrylic acids, dialkyl
acetylenedicarboxylates and isocyanides. The reaction pathway involves
Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm
rearrangement and an oxo-Diels-Alder reaction sequence, resulting in
continuous multiple bond-forming events including C-N, C-O and C-H bonds
to rapidly build up molecular complexity.
AB - A novel three-component bicyclization strategy for the efficient
synthesis of densely functionalized pyrano[3,4-c]pyrroles has been
established from readily accessible 3-aroylacrylic acids, dialkyl
acetylenedicarboxylates and isocyanides. The reaction pathway involves
Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm
rearrangement and an oxo-Diels-Alder reaction sequence, resulting in
continuous multiple bond-forming events including C-N, C-O and C-H bonds
to rapidly build up molecular complexity.
M3 - Article
SP - 900
EP - 903
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
ER -