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Oxindole‐chromones C3 Synthons Directed Stereocontrolled Construction of Five Contiguous Stereocenters on Spiro[tetrahydrocyclopenta[b]chromanone‐oxindole]s
Author(s) -
Xu ShengWen,
Liu XiongWei,
Zuo Xiong,
Zhou Gen,
Gong Yi,
Liu XiongLi,
Zhou Ying
Publication year - 2019
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.201901091
Subject(s) - synthon , stereocenter , oxindole , chemistry , bifunctional , chromone , yield (engineering) , stereochemistry , organocatalysis , cycloaddition , enantioselective synthesis , catalysis , combinatorial chemistry , organic chemistry , materials science , metallurgy
The first example of bifunctional oxindole‐chromone C3 synthon directed organocatalytic cascade cycloaddition reaction is developed, serving as a fruitful strategy for the facile access of optically active tetrahydrocyclopenta[b]chromanone bearing one spirooxindole with five contiguous stereocenters. All the products are smoothly obtained with up to 83% yield, >20:1 d.r. and >99% ee. This is also the first asymmetric catalytic construction of tetrahydrocyclopenta[b] chromanone and tetrahydrocyclopenta[b]chromanone‐spirooxindole scaffold, thus to facilitate the search for new bioactive entities.