Literature DB >> 21796320

A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles.

Matilde Senatore1, Alessandra Lattanzi, Stefano Santoro, Claudio Santi, Giorgio Della Sala.   

Abstract

The first example of meso-aziridine desymmetrization with selenium nucleophiles is reported. The reaction, promoted by VAPOL-hydrogen phosphate using (phenylseleno)trimethylsilane as the nucleophile, proves to be very general and highly enantioselective (84-99% ee).

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Year:  2011        PMID： 21796320     DOI： 10.1039/c1ob05837a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  6 in total

1.  Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

Authors:  Yong Guan; Zhensheng Ding; William D Wulff
Journal:  Chemistry       Date:  2013-10-02       Impact factor: 5.236

2.  Palladium-Catalyzed, Enantioselective Heine Reaction.

Authors:  Molly Punk; Charlotte Merkley; Katlyn Kennedy; Jeremy B Morgan
Journal:  ACS Catal       Date:  2016-06-15       Impact factor: 13.084

3.  Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds.

Authors:  Nitin S Dange; Jacob R Stepherson; Caitlan E Ayala; Frank R Fronczek; Rendy Kartika
Journal:  Chem Sci       Date:  2015-07-22       Impact factor: 9.825

4.  Identifying the true origins of selectivity in chiral phosphoric acid catalyzed N-acyl-azetidine desymmetrizations.

Authors:  Pier Alexandre Champagne
Journal:  Chem Sci       Date:  2021-11-23       Impact factor: 9.825

Review 5.  Organocatalyzed enantioselective desymmetrization of aziridines and epoxides.

Authors:  Ping-An Wang
Journal:  Beilstein J Org Chem       Date:  2013-08-15       Impact factor: 2.883

6.  Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.

Authors:  Xin Zhang; Richard J Staples; Arnold L Rheingold; William D Wulff
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
  6 in total

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