Literature DB >> 15069504

SN2 vs. E2 on quaternary centres: an application to the synthesis of enantiopure beta2,2-amino acids.

Alberto Avenoza1, Jesús H Busto, Francisco Corzana, Gonzalo Jiménez-Osés, Jesús M Peregrina.   

Abstract

S(N)2 and E2 competing reactions in cyclic sulfamidates can be modulated by the change of an amide group to an ester group attached to the quaternary carbon activated for the nucleophilic attack, allowing an easy approach to enantiopure alpha,alpha-disubstituted beta-amino acids.

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Year:  2004        PMID： 15069504     DOI： 10.1039/b400282b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  4 in total

1.  Asymmetric synthesis of tertiary thiols and thioethers.

Authors:  Jonathan Clayden; Paul Maclellan
Journal:  Beilstein J Org Chem       Date:  2011-05-10       Impact factor: 2.883

2.  Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α-Oxy- and α-Thio-Substituted Organolithium Species.

Authors:  Alexander P Pulis; Ana Varela; Cinzia Citti; Pradip Songara; Daniele Leonori; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-07       Impact factor: 15.336

3.  Enantioselective Catalytic Synthesis of α-Halogenated α-Aryl-β2,2-amino Acid Derivatives.

Authors:  Paul Zebrowski; Isabella Eder; Andreas Eitzinger; Sharath Chandra Mallojjala; Mario Waser
Journal:  ACS Org Inorg Au       Date:  2021-09-24

4.  Synthesis of β2,2-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates.

Authors:  Pablo Tovillas; Claudio D Navo; Paula Oroz; Alberto Avenoza; Francisco Corzana; María M Zurbano; Gonzalo Jiménez-Osés; Jesús H Busto; Jesús M Peregrina
Journal:  J Org Chem       Date:  2022-06-22       Impact factor: 4.198
  4 in total

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