Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

Xu, Qing; Zhou, Hui; Geng, Xiaohong; Chen, Peiran

doi:10.1016/j.tet.2009.01.058

Cited by 57 publications

(18 citation statements)

References 34 publications

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“…Propionic and isobutyric anhydrides were identified as the best acylating reagents in Birman's studies. Shiina and collaborators found a protocol to expand the scope of the anhydride employed in the enantioselective KR of benzylic alcohols catalyzed by BTM ( 4 ).…”

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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“…For the synthesis of 1-substituted 2,2,2-trifluoroethanols from ketones, see: Yamazaki et al (1993). For the enzymatic kinetic resolution of 1-substituted 2,2,2-trifluoroethanols, see: Omote et al (2001); Xu et al (2009). For the utilization of cinchonidine as a chiral solvating reagent, see: Kolodyazhnyi et al (2006) Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of (S)-1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanol

Shishkina

Kucher²,

Kolodiazhnaya³

et al. 2014

Acta Cryst E

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“…For example, an umbero fLewis base organocatalysts have been utilized for the acylativeK Ro fa lkenyl-alkyl (sp 2 vs. sp 3 )a llylic alcohols (Figure 1b). [2][3][4][5][6][7] Fu used planar-chiral DMAP-derived ferrocene catalyst 1 and acetic anhydride for the KR of ar ange of allylic alcohols, including two that had served as intermediates in natural product synthesis, with high selectivity factors, S (up to 80). [2] Vedejs has also achievedh igh selectivity for the KR of allylic alcohols using chiral phosphine 2 and isobutyric anhydride (S up to 82).…”

Section: Introductionmentioning

confidence: 99%

“…In these systems the acylating agent must differentiate between the enantiomers of alcohols with a planar π‐system and a tetrahedral sp 3 hybridized substituent. For example, a number of Lewis base organocatalysts have been utilized for the acylative KR of alkenyl–alkyl (sp 2 vs. sp 3 ) allylic alcohols (Figure b) . Fu used planar‐chiral DMAP‐derived ferrocene catalyst 1 and acetic anhydride for the KR of a range of allylic alcohols, including two that had served as intermediates in natural product synthesis, with high selectivity factors, S (up to 80) .…”

Section: Introductionmentioning

confidence: 99%

Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp² vs. sp²) Substituted Secondary Alcohols

Musolino

Ojo

Westwood

et al. 2016

Chemistry A European J

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The non-enzymatic acylative kineticr esolutiono f challenging aryl-alkenyl (sp 2 vs. sp 2 )s ubstituted secondary alcohols is described,w ith effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of aw ide range of aryl-alkenyls ubstituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highests electivity( S = 2-1980). The use of this protocolf or the gram-scale (2.5 g) kinetic resolution of am odel aryl-vinyl (sp 2 vs. sp 2 )s ubstituted secondary alcohol is demonstrated, giving access to > 1gof each of the product enantiomers both in 99:1 e.r.

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Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

Cited by 57 publications

References 34 publications

Enantioselective Catalysis by Chiral Isothioureas

Enantioselective Catalysis by Chiral Isothioureas

Crystal structure of (S)-1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanol

Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp² vs. sp²) Substituted Secondary Alcohols

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Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

Cited by 57 publications

References 34 publications

Enantioselective Catalysis by Chiral Isothioureas

Enantioselective Catalysis by Chiral Isothioureas

Crystal structure of (S)-1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanol

Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2 vs. sp2) Substituted Secondary Alcohols

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Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp² vs. sp²) Substituted Secondary Alcohols