Literature DB >> 21858308

Electron transfer reduction of unactivated esters using SmI2-H2O.

Michal Szostak1, Malcolm Spain, David J Procter.   

Abstract

The reduction of unactivated esters using samarium diiodide is reported for the first time. The optimised protocol allows for the reduction of primary, secondary and tertiary alkyl esters in excellent yields and is competitive with reductions mediated by metal hydrides and alkali metals. This journal is © The Royal Society of Chemistry 2011

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Year:  2011        PMID： 21858308     DOI： 10.1039/c1cc14014k

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


  9 in total

1.  Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Nat Protoc       Date:  2012-04-26       Impact factor: 13.491

2.  Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates.

Authors:  Hannah Shenouda; Erik J Alexanian
Journal:  Org Lett       Date:  2019-11-05       Impact factor: 6.005

3.  On the role of pre- and post-electron-transfer steps in the SmI2 /amine/H(2)O-mediated reduction of esters: new mechanistic insights and kinetic studies.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Chemistry       Date:  2014-03-11       Impact factor: 5.236

4.  Selective reduction of barbituric acids using SmI2/H2O: synthesis, reactivity, and structural analysis of tetrahedral adducts.

Authors:  Michal Szostak; Brice Sautier; Malcolm Spain; Maike Behlendorf; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-09       Impact factor: 15.336

5.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336

6.  Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)2-catalyzed cycloisomerization and SmI2-induced ring expansion.

Authors:  Kunihiro Matsumura; Keisuke Nishikawa; Hiroaki Yoshida; Matsumi Doe; Yoshiki Morimoto
Journal:  RSC Adv       Date:  2018-03-21       Impact factor: 3.361

7.  Diastereoselective Radical 1,4-Ester Migration: Radical Cyclizations of Acyclic Esters with SmI2.

Authors:  Charlotte Morrill; Áron Péter; Ilma Amalina; Emma Pye; Giacomo E M Crisenza; Nikolas Kaltsoyannis; David J Procter
Journal:  J Am Chem Soc       Date:  2022-07-20       Impact factor: 16.383

8.  Development of an additive-controlled, SmI2-mediated stereoselective sequence: Telescoped spirocyclisation, lactone reduction and Peterson elimination.

Authors:  Brice Sautier; Karl D Collins; David J Procter
Journal:  Beilstein J Org Chem       Date:  2013-07-18       Impact factor: 2.883

9.  Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions.

Authors:  Michal Szostak; Malcolm Spain; Andrew J Eberhart; David J Procter
Journal:  J Am Chem Soc       Date:  2014-01-31       Impact factor: 15.419
  9 in total

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