Bianthryl-based organocatalysts for the asymmetric Henry
reaction of fluoroketones

J 2019

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽ

Basic information

Original name

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Authors

OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽ

Edition

ORGANIC & BIOMOLECULAR CHEMISTRY, CAMBRIDGE, ROYAL SOC CHEMISTRY, 2019, 1477-0520

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.412

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.1039/c9ob00884e

UT WoS

000471015200006

Keywords in English

CATALYSTS; EFFICIENT; AMINES

Abstract

V originále

We have developed a catalytic system based on bianthrylbis (thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3 : 2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.

Citovat

OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽ. Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones. ORGANIC & BIOMOLECULAR CHEMISTRY. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2019, vol. 17, No 21, p. 5244-5248. ISSN 1477-0520. Available from: https://dx.doi.org/10.1039/c9ob00884e.

@article{1726933,
   author = {Otevřel, Jan and Švestka, David and Bobáľ, Pavel},
   article_location = {CAMBRIDGE},
   article_number = {21},
   doi = {http://dx.doi.org/10.1039/c9ob00884e},
   keywords = {CATALYSTS; EFFICIENT; AMINES},
   language = {eng},
   issn = {1477-0520},
   journal = {ORGANIC & BIOMOLECULAR CHEMISTRY},
   title = {Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones},
   url = {https://pubs.rsc.org/en/content/articlelanding/2019/OB/C9OB00884E},
   volume = {17},
   year = {2019}
}

TY  - JOUR
ID  - 1726933
AU  - Otevřel, Jan - Švestka, David - Bobáľ, Pavel
PY  - 2019
TI  - Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones
JF  - ORGANIC & BIOMOLECULAR CHEMISTRY
VL  - 17
IS  - 21
SP  - 5244-5248
EP  - 5244-5248
PB  - ROYAL SOC CHEMISTRY
SN  - 14770520
KW  - CATALYSTS
KW  - EFFICIENT
KW  - AMINES
UR  - https://pubs.rsc.org/en/content/articlelanding/2019/OB/C9OB00884E
N2  - We have developed a catalytic system based on bianthrylbis (thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3 : 2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.
ER  -

OTEVŘEL, Jan, David ŠVESTKA and Pavel BOBÁĽ. Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones. \textit{ORGANIC \&{} BIOMOLECULAR CHEMISTRY}. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2019, vol.~17, No~21, p.~5244-5248. ISSN~1477-0520. Available from: https://dx.doi.org/10.1039/c9ob00884e.

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