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Concise Pathway to New Multifunctionalized Constrained Pentacin Derivatives by Means of Two Stereospecific Tandem Reactions
Author(s) -
Coursindel Thibault,
Martinez Jean,
Parrot Isabelle
Publication year - 2011
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.201100593
Subject(s) - chemistry , stereospecificity , pyrrolidine , tandem , alkylation , stereoselectivity , stereochemistry , bicyclic molecule , alicyclic compound , combinatorial chemistry , ring (chemistry) , cascade reaction , organic chemistry , catalysis , materials science , composite material
Starting from Boc‐activated diketopiperazines, original bicyclic derivatives of trans ‐ and cis ‐2‐aminocyclopentanecarboxylic acid were prepared by using two stereospecific tandem reactions. One of them is a tandem transannular rearrangement of activated lactams/alkylation process leading to the stereoselective synthesis of suitably chiral pyrrolidine‐2,4‐diones, allowing subsequent Michael‐initiated ring closure, a simple and concise route to original multifunctionalized alicyclic β‐amino esters.