Literature DB >> 16190680

Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition-elimination of activated allylic acetates under chiral PTC conditions.

P Veeraraghavan Ramachandran1, Sateesh Madhi, Layla Bland-Berry, M Venkat Ram Reddy, Martin J O'Donnell.   

Abstract

A new, general, and practical procedure for the asymmetric synthesis of 4-alkylidenyl glutamic acid derivatives via a catalytic enantioselective tandem conjugate addition-elimination on allylic acetates under chiral phase-transfer conditions is reported. A variety of structural types of allylic acetates have been reacted with the benzophenone imine of glycine tert-butyl ester to give the products in good to excellent yields and enantioselectivities (63-92% yield, 80-97% ee, 8 cases).

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Year:  2005        PMID： 16190680     DOI： 10.1021/ja052638m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K.

Authors:  Ji Qi; Aaron B Beeler; Qiang Zhang; John A Porco
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

2.  Reversible proton coupled electron transfer in a peptide-incorporated naphthoquinone amino acid.

Authors:  Bruce R Lichtenstein; José F Cerda; Ronald L Koder; P Leslie Dutton
Journal:  Chem Commun (Camb)       Date:  2008-11-25       Impact factor: 6.222

3.  Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

Authors:  Vito Capaccio; Katharina Zielke; Andreas Eitzinger; Antonio Massa; Laura Palombi; Kirill Faust; Mario Waser
Journal:  Org Chem Front       Date:  2018-10-12       Impact factor: 5.281

4.  Free radical-mediated aryl amination: convergent two- and three-component couplings to chiral 2,3-disubstituted indolines.

Authors:  Rajesh Viswanathan; Colin R Smith; Erode N Prabhakaran; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2008-03-20       Impact factor: 4.198

5.  Distributed Drug Discovery, Part 2: global rehearsal of alkylating agents for the synthesis of resin-bound unnatural amino acids and virtual D(3) catalog construction.

Authors:  William L Scott; Jordi Alsina; Christopher O Audu; Evgenii Babaev; Linda Cook; Jeffery L Dage; Lawrence A Goodwin; Jacek G Martynow; Dariusz Matosiuk; Miriam Royo; Judith G Smith; Andrew T Strong; Kirk Wickizer; Eric M Woerly; Ziniu Zhou; Martin J O'Donnell
Journal:  J Comb Chem       Date:  2009 Jan-Feb

6.  Methylene-bridged bis(imidazoline)-derived 2-oxopyrimidinium salts as catalysts for asymmetric Michael reactions.

Authors:  Andrey E Sheshenev; Ekaterina V Boltukhina; Andrew J P White; King Kuok Mimi Hii
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-27       Impact factor: 15.336
  6 in total

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