TY - JOUR
T1 - Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[
T2 - B] [1,5]oxazocine heterocycles
AU - Gurubrahamam, Ramani
AU - Nagaraju, Koppanathi
AU - Chen, Kwunmin
N1 - Funding Information:
We thank the Ministry of Science and Technology of the Republic of China (MOST 106-2113-M-003-013-) for financial support of this work.
PY - 2018/1/1
Y1 - 2018/1/1
N2 - Metal-free addition of salicylhydrazones to electron deficient internal alkynes catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield oxa-bridged 2,6-epoxybenzo[b][1,5]oxazocine heterocycles was achieved. The demonstrated protocol proceeds through an o-quinone methide formation, aza-Michael addition, stereoselective protonation, enamine promoted aromatization, O,O-acetalization and O,N-aminalization sequence to provide privileged heterocycles in good yields with high diastereoselectivities.
AB - Metal-free addition of salicylhydrazones to electron deficient internal alkynes catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield oxa-bridged 2,6-epoxybenzo[b][1,5]oxazocine heterocycles was achieved. The demonstrated protocol proceeds through an o-quinone methide formation, aza-Michael addition, stereoselective protonation, enamine promoted aromatization, O,O-acetalization and O,N-aminalization sequence to provide privileged heterocycles in good yields with high diastereoselectivities.
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U2 - 10.1039/c8cc02565g
DO - 10.1039/c8cc02565g
M3 - Article
AN - SCOPUS:85048371773
VL - 54
SP - 6048
EP - 6051
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 47
ER -