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Spirobicyclic and Tetracyclic Pyrazolidinones: Syntheses and Properties
Author(s) -
Perez Fabien,
Leveille Thibault,
Bertolotti Mathilde,
Rodriguez Jean,
Coquerel Yoann
Publication year - 2019
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.201900989
Subject(s) - enantiopure drug , annulation , stereoselectivity , cycloaddition , iminium , chemistry , molecule , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
The stereoselective syntheses of spirobicyclic and tetracyclic pyrazolidinones are reported based on a (3+2) annulation between hydrazones and α‐oxoketenes. Some of these conformationally constrained molecules were resolved as enantiopure materials by HPLC techniques and evaluated as aminocatalysts for iminium activation in a model Diels–Alder cycloaddition.