Premium
Chiral Squaramide‐Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro‐Spirocyclopropanes
Author(s) -
Zhao BoLiang,
Du DaMing
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500533
Subject(s) - squaramide , stereocenter , chemistry , enantioselective synthesis , alkylation , cyclopropanation , diastereomer , michael reaction , cascade reaction , nitro , organocatalysis , enantiomer , catalysis , enantiomeric excess , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
A new diastereoselective and enantioselective cyclopropanation reaction has been developed by employing a Michael/alkylation cascade reaction between ( E )‐3‐arylenechroman‐4‐one or ( E )‐2‐arylideneindan‐1‐one derivatives and a bromonitroalkane with a chiral squaramide catalyst. This reaction constitutes a facile asymmetric synthesis for nitro‐spirocyclopropanes that have three adjacent stereogenic centers, including one quaternary center, in moderate to good yields (up to 90 %) with excellent enantio‐ [up to >99 % ee (enantiomeric excess)] and diastereoselectivities [up to >99:1 dr (diastereomeric ratio)].