Literature DB >> 26146482

Iron(II)-Catalyzed Asymmetric Epoxidation of Trisubstituted α,β-Unsaturated Esters.

Lan Luo1, Hisashi Yamamoto2.   

Abstract

An asymmetric epoxidation of trisubstituted α,β-unsaturated esters is described. The oxidation utilizes a pseudo-C2-symmetric iron(II) catalyst [Fe(L*)2(CH3CN)(OTf)](OTf) and peracetic acid as oxidant, yielding the α,β-epoxyesters in high enantiomeric purity (up to 99% ee).

Entities:  

Keywords:  asymmetric epoxidation; iron; α, β-unsaturated ester

Year:  2014        PMID： 26146482      PMCID： PMC4486291          DOI： 10.1002/ejoc.201403220

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  6 in total

1.  Catalytic asymmetric epoxidation of alpha,beta-unsaturated esters using an yttrium-biphenyldiol complex.

Authors:  Hiroyuki Kakei; Riichiro Tsuji; Takashi Ohshima; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

2.  Mechanism and conditions for highly enantioselective epoxidation of alpha,beta-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt.

Authors:  E J Corey; F Y Zhang
Journal:  Org Lett       Date:  1999-10-21       Impact factor: 6.005

3.  Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones.

Authors:  Yasuhiro Nishikawa; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2011-05-16       Impact factor: 15.419

Review 4.  Enantioselective epoxidation of electron-deficient olefins: an organocatalytic approach.

Authors:  Katharina M Weiss; Svetlana B Tsogoeva
Journal:  Chem Rec       Date:  2010-11-30       Impact factor: 6.771

5.  Highly enantioselective epoxidation of alpha, beta-unsaturated esters by chiral dioxirane.

Authors:  Xin-Yan Wu; Xuegong She; Yian Shi
Journal:  J Am Chem Soc       Date:  2002-07-31       Impact factor: 15.419

6.  Asymmetric epoxidation with H2O2 by manipulating the electronic properties of non-heme iron catalysts.

Authors:  Olaf Cussó; Isaac Garcia-Bosch; Xavi Ribas; Julio Lloret-Fillol; Miquel Costas
Journal:  J Am Chem Soc       Date:  2013-09-23       Impact factor: 15.419
  6 in total
  1 in total

1.  A Bottom Up Approach Towards Artificial Oxygenases by Combining Iron Coordination Complexes and Peptides.

Authors:  Olaf Cusso; Michael W Giuliano; Xavi Ribas; Scott J Miller; Miquel Costas
Journal:  Chem Sci       Date:  2017-03-03       Impact factor: 9.825
  1 in total

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