Literature DB >> 12735758

Titanium-catalyzed stereoselective geminal heterodihalogenation of beta-ketoesters.

Richard Frantz1, Lukas Hintermann, Mauro Perseghini, Diego Broggini, Antonio Togni.   

Abstract

[reaction: see text] beta-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl(3) as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl(2)(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of beta-ketoesters with F-TEDA and NCS to afford alpha-chloro-alpha-fluoro-beta-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.

Entities:  

Year:  2003        PMID： 12735758     DOI： 10.1021/ol0343459

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Stereoselective synthesis of alpha,alpha-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers.

Authors:  Kazutaka Shibatomi; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination.

Authors:  Coralie De Schutter; Ozkan Sari; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  J Org Chem       Date:  2017-12-04       Impact factor: 4.354

3.  Expanding the scope of asymmetric electrophilic atom-transfer reactions: titanium- and ruthenium-catalyzed hydroxylation of beta-ketoesters.

Authors:  Patrick Y Toullec; Cristina Bonaccorsi; Antonio Mezzetti; Antonio Togni
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-07       Impact factor: 11.205

Review 4.  Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors:  Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal:  Chem Rev       Date:  2018-04-02       Impact factor: 60.622

5.  Development of the titanium-TADDOLate-catalyzed asymmetric fluorination of β-ketoesters.

Authors:  Lukas Hintermann; Mauro Perseghini; Antonio Togni
Journal:  Beilstein J Org Chem       Date:  2011-10-17       Impact factor: 2.883

Review 6.  Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.

Authors:  Xiaoyu Yang; Tao Wu; Robert J Phipps; F Dean Toste
Journal:  Chem Rev       Date:  2014-10-22       Impact factor: 60.622

Review 7.  Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.

Authors:  Jianlin Han; Greg Butler; Hiroki Moriwaki; Hiroyuki Konno; Vadim A Soloshonok; Tsugio Kitamura
Journal:  Molecules       Date:  2020-04-30       Impact factor: 4.411

8.  Stereoselective alpha-fluoroamide and alpha-fluoro-gamma-lactone synthesis by an asymmetric zwitterionic aza-Claisen rearrangement.

Authors:  Kenny Tenza; Julian S Northen; David O'Hagan; Alexandra M Z Slawin
Journal:  Beilstein J Org Chem       Date:  2005-10-17       Impact factor: 2.883

9.  DBFOX-Ph/metal complexes: evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones.

Authors:  Takehisa Ishimaru; Norio Shibata; Dhande Sudhakar Reddy; Takao Horikawa; Shuichi Nakamura; Takeshi Toru
Journal:  Beilstein J Org Chem       Date:  2008-05-20       Impact factor: 2.883
  9 in total

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