Literature DB >> 19421434

Organocatalyzed direct asymmetric alpha-halogenation of carbonyl compounds.

Mitsuhiro Ueda1, Taichi Kano, Keiji Maruoka.   

Abstract

The formation of carbon-halogen bonds in an enantioselective manner is an important reaction because it leads to optically active halogen compounds, which are useful intermediates for further elaboration to other valuable compounds. Within the past few years various enantioselective alpha-halogenations of carbonyl compounds by asymmetric organocatalysis have been reported. Most importantly, these recent developments have greatly enhanced the synthetic utility of alpha-halogenations and opened up a promising new frontier in organic synthesis.

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Year:  2009        PMID: 19421434     DOI: 10.1039/b901449g

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


  10 in total

1.  Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Authors:  Susumu Oda; Hisashi Yamamoto
Journal:  Org Lett       Date:  2013-11-08       Impact factor: 6.005

2.  N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of alpha-protio and alpha-deuterio alpha-chloro and alpha-fluoro carboxylic acids.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

Review 3.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

4.  Palladium-Catalyzed Enantioselective Csp3-Csp3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks.

Authors:  Yanhui Lu; Elizabeth L Goldstein; Brian M Stoltz
Journal:  Org Lett       Date:  2018-09-05       Impact factor: 6.005

Review 5.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

6.  Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis.

Authors:  Richard Y Liu; Masayuki Wasa; Eric N Jacobsen
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

Review 7.  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

8.  Enantioselective decarboxylative chlorination of β-ketocarboxylic acids.

Authors:  Kazutaka Shibatomi; Kazumasa Kitahara; Nozomi Sasaki; Yohei Kawasaki; Ikuhide Fujisawa; Seiji Iwasa
Journal:  Nat Commun       Date:  2017-06-05       Impact factor: 14.919

Review 9.  Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Authors:  Johannes Schörgenhumer; Maximilian Tiffner; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2017-08-22       Impact factor: 2.883

10.  Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions.

Authors:  Lotte Stockhammer; David Weinzierl; Thomas Bögl; Mario Waser
Journal:  Org Lett       Date:  2021-07-28       Impact factor: 6.005

  10 in total

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