Chiral Squaramide‐Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro‐Spirocyclopropanes | Zendy

Zhao BoLiang | Zendy; Du DaMing | Zendy

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)].

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research