Transannular Rearrangement of Activated Lactams: Stereoselective Synthesis of Substituted Pyrrolidine‐2,4‐diones from Diketopiperazines | Zendy

Farran Daniel | Zendy; Parrot Isabelle | Zendy; Martinez Jean | Zendy; Dewynter Georges | Zendy

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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.

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