A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids

Tengeiji, Atsushi; Shiina, Isamu

doi:10.3390/molecules17067356

Cited by 14 publications

(10 citation statements)

References 22 publications

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“…High s values were obtained, especially when the aryl group is ortho ‐substituted. Shiina's group also extended this approach to 2‐aryl‐2‐fluoropropanoic acids, leading to optically active carboxylic acids, each containing a quaternary stereocenter in the α‐position to the carboxyl group, with s values of up to 242.…”

Section: Itu‐catalyzed Reactions Involving Chiral Acylisothiouronimentioning

confidence: 99%

Enantioselective Catalysis by Chiral Isothioureas

et al. 2016

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International audienceThis review covers recent developments relating to organocatalyzed transformations by chiral isothioureas (ITUs) since their original introduction by Birman in 2006. This class of nucleophilic heterocycles was first involved in anhydride activation in enantioselective acyl transfer reactions, but it was more recently shown that activation of other reagents was possible, considerably enlarging their number of catalytic enantioselective transformations. Four main modes of activation as Lewis bases can currently be listed: (1) acylisothiouronium intermediates involved in acyl transfer, (2) silylisothiouronium species involved in silyl transfer, (3) acylisothiouronium enolates involved in several concerted and formal pericyclic transformations, and (4) α,_-unsaturated acylisothiouronium species involved in domino transformations. This review is organized according to these different modes of activation of chiral isothioureas

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Section: Itu‐catalyzed Reactions Involving Chiral Acylisothiouronimentioning

confidence: 99%

Enantioselective Catalysis by Chiral Isothioureas

et al. 2016

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“…However, to the best of our knowledge, a general method for the kinetic resolution of racemic 2-hydroxyamide derivatives has not been reported to date. We recently accomplished the first KR of racemic alcohols with achiral carboxylic acids and of racemic carboxylic acids with achiral alcohols by asymmetric esterification [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ] via the in situ formation of a mixed anhydride using carboxylic anhydrides as coupling reagents combined with chiral acyl-transfer catalysts. Furthermore, KR of racemic 2-hydroxyalkanoates with diphenylacetic acid was achieved using pivalic anhydride in the presence of ( R )-benzotetramisole [ 27 , 28 ] (( R )-BTM; Scheme 1 ; (i)).…”

Section: Introductionmentioning

confidence: 99%

Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

et al. 2018

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Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiary amide can be used with this novel protocol to achieve high selectivity (22 examples; s-value reaching over 250). The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality.

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“… 5 , 6 To the best of our knowledge, no general catalytic enantioselective process has been discovered for the synthesis of simple tertiary α-fluorinated acyclic ketones. 7 − 9 …”

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones

Liang

2014

J. Am. Chem. Soc.

170

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The development of new approaches to the construction of fluorine-containing target molecules is important for a variety of scientific disciplines, including medicinal chemistry. In this Article, we describe a method for the catalytic enantioselective synthesis of tertiary alkyl fluorides through Negishi reactions of racemic α-halo-α-fluoroketones, which represents the first catalytic asymmetric cross-coupling that employs geminal dihalides as electrophiles. Thus, selective reaction of a C–Br (or C–Cl) bond in the presence of a C–F bond can be achieved with the aid of a nickel/bis(oxazoline) catalyst. The products of the stereoconvergent cross-couplings, enantioenriched tertiary α-fluoroketones, can be converted into an array of interesting organofluorine compounds.

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A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids

Cited by 14 publications

References 22 publications

Enantioselective Catalysis by Chiral Isothioureas

Enantioselective Catalysis by Chiral Isothioureas

Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones

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