TY - JOUR
T1 - Organocatalytic formal [5+1] annulation
T2 - Diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael-aldol reaction
AU - Roy, Suparna
AU - Amireddy, Mamatha
AU - Chen, Kwunmin
N1 - Funding Information:
We thank the National Science Council of the Republic of China (NSC 99-2113-M-003-002-MY3 ) for its financial support of our work. Our gratitude extends to the Academic Paper Editing Clinic at NTNU.
PY - 2013/10/14
Y1 - 2013/10/14
N2 - An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.
AB - An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30-84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael-aldol reaction.
KW - Cascade Michael-aldol Oxindole Diastereoselectivity
UR - http://www.scopus.com/inward/record.url?scp=84883195511&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84883195511&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2013.07.084
DO - 10.1016/j.tet.2013.07.084
M3 - Article
AN - SCOPUS:84883195511
VL - 69
SP - 8751
EP - 8757
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 41
ER -