New Hybrid-type Squaramide-Fused Amino Alcohol Organocatalyst for Enantioselective Domino Michael Addition/Cyclization Reaction of Oxoindolines with Cyclic 1,3-Diketones | Zendy

Madhu Chennapuram | Zendy; Isiaka Alade Owolabi | Zendy; Chigusa Seki | Zendy; Yuko Okuyama | Zendy; Eunsang Kwon | Zendy; Koji Uwai | Zendy; Michio Tokiwa | Zendy; Mitsuhiro Takeshita | Zendy; Hiroto Nakano | Zendy

Open Access

New Hybrid-type Squaramide-Fused Amino Alcohol Organocatalyst for Enantioselective Domino Michael Addition/Cyclization Reaction of Oxoindolines with Cyclic 1,3-Diketones

Author(s) -

Madhu Chennapuram,

Isiaka Alade Owolabi,

Chigusa Seki,

Yuko Okuyama,

Eunsang Kwon,

Koji Uwai,

Michio Tokiwa,

Mitsuhiro Takeshita,

Hiroto Nakano

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b01271

Subject(s) - squaramide , stereocenter , enantioselective synthesis , chemistry , michael reaction , organocatalysis , domino , conjugated system , cascade reaction , alcohol , catalysis , combinatorial chemistry , organic chemistry , stereochemistry , polymer

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research