Concise Pathway to New Multifunctionalized Constrained Pentacin Derivatives by Means of Two Stereospecific Tandem Reactions | Zendy

Coursindel Thibault | Zendy; Martinez Jean | Zendy; Parrot Isabelle | Zendy

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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.

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