Premium
Stereoselective Synthesis of Hydropyrano[3,2‐ b ]indoles via Organocatalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction
Author(s) -
Yang Lei,
Huang Wei,
He XiangHong,
Yang MingCheng,
Li Xiang,
He Gu,
Peng Cheng,
Han Bo
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600465
Subject(s) - chemistry , yield (engineering) , stereoselectivity , catalysis , enantioselective synthesis , organocatalysis , amine gas treating , inverse , organic chemistry , stereochemistry , combinatorial chemistry , materials science , geometry , mathematics , metallurgy
Enantio‐ and diastereoselective inverse‐electron‐demand oxa‐Diels–Alder reactions are described between ( Z )‐2‐ylideneoxindoles and aldehydes in the presence of a chiral secondary amine catalyst. The corresponding hydropyrano[3,2‐ b ]indoles are produced in up to 77% yield with up to 99% ee . Convenient synthetic transformations of the products readily lead to pharmacologically interesting scaffolds bearing multiple functional groups. This method may also provide an alternative approach for the asymmetric synthesis of 2‐spirocyclo‐3‐oxindoles.