Premium
Asymmetric Michael Addition of Oxindoles to Allenoate Catalyzed by N ‐Acyl Aminophosphine: Construction of Functionalized Oxindoles with Quaternary Stereogenic Center
Author(s) -
Chen Jinhao,
Cai Yuepeng,
Zhao Gang
Publication year - 2014
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.201300695
Subject(s) - stereocenter , bifunctional , chemistry , catalysis , quaternary carbon , yield (engineering) , adduct , enantioselective synthesis , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
A novel reaction between ethyl allenoate and oxindoles that enables the asymmetric synthesis of 3,3‐bisubstituted oxindoles with our previously established bifunctional N ‐acyl aminophosphine catalysts is reported. These products bearing a chiral quaternary carbon center at the C‐3 position of the oxindoles may have potential significance in the synthesis of related structures. The best performance of these processes provides adducts with 92% yield and 94% ee .