TY - JOUR
T1 - New Hybrid-type Squaramide-Fused Amino Alcohol Organocatalyst for Enantioselective Domino Michael Addition/Cyclization Reaction of Oxoindolines with Cyclic 1,3-Diketones
AU - Chennapuram, Madhu
AU - Owolabi, Isiaka Alade
AU - Seki, Chigusa
AU - Okuyama, Yuko
AU - Kwon, Eunsang
AU - Uwai, Koji
AU - Tokiwa, Michio
AU - Takeshita, Mitsuhiro
AU - Nakano, Hiroto
N1 - Funding Information:
We thank the Adaptable & Seamless Technology Transfer Program through Target-Driven R&D of the Japan Science and Technology (JST) (AS231Z01382G and AS221Z01186D) for partial financial support of this research.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/9/30
Y1 - 2018/9/30
N2 - The new hybrid-type squaramide-fused amino alcohol containing both a Brønsted basic site and hydrogen-bonding sites in the molecule showed a high catalytic activity as an organocatalyst in the enantioselective domino Michael addition/cyclization reaction of oxoindolines with cyclic 1,3-diketones to afford the chiral spiro-conjugated oxindoles featuring 2-aminopyrans fusing with carbo-heterocyclic ring systems with excellent chemical yields (up to 98%) and enantioselectivities (up to 95% ee). The obtained chiral spiro-conjugated 2-aminopyrans bearing quaternary stereogenic carbon center could be used as synthetic precursors for several natural products that have a broad spectrum of fascinating biological activities.
AB - The new hybrid-type squaramide-fused amino alcohol containing both a Brønsted basic site and hydrogen-bonding sites in the molecule showed a high catalytic activity as an organocatalyst in the enantioselective domino Michael addition/cyclization reaction of oxoindolines with cyclic 1,3-diketones to afford the chiral spiro-conjugated oxindoles featuring 2-aminopyrans fusing with carbo-heterocyclic ring systems with excellent chemical yields (up to 98%) and enantioselectivities (up to 95% ee). The obtained chiral spiro-conjugated 2-aminopyrans bearing quaternary stereogenic carbon center could be used as synthetic precursors for several natural products that have a broad spectrum of fascinating biological activities.
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U2 - 10.1021/acsomega.8b01271
DO - 10.1021/acsomega.8b01271
M3 - Article
AN - SCOPUS:85053882209
SN - 2470-1343
VL - 3
SP - 11718
EP - 11726
JO - ACS Omega
JF - ACS Omega
IS - 9
ER -