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Transannular Rearrangement of Activated Lactams: Stereoselective Synthesis of Substituted Pyrrolidine‐2,4‐diones from Diketopiperazines
Author(s) -
Farran Daniel,
Parrot Isabelle,
Martinez Jean,
Dewynter Georges
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702132
Subject(s) - diketopiperazines , pyrrolidine , stereoselectivity , chemistry , alkyl , reactivity (psychology) , reagent , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The surprising reactivity under basic conditions of 2,5‐diketopiperazines activated by N ‐Boc substituents provides a highly stereoselective pathway to pyrrolidine‐2,4‐diones. A wide range of valuable pharmaceutical scaffolds can be synthesized by adding an alkylating reagent during the course of the reaction (see scheme). R 1 =alkyl; R 2 =alkyl, benzyl; Boc= tert ‐butoxycarbonyl.