ChemInform Abstract: Asymmetric Nucleophilic Monofluorobenzylation of Carbonyl Compounds: Synthesis...
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ChemInform 2012, 43, issue 01 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Alcohols Q 0230 DOI: 10.1002/chin.201236055 Asymmetric Nucleophilic Monofluorobenzylation of Carbonyl Compounds: Synthesis of Enantiopure vic-Fluorohydrins and α-Fluorobenzylketones. — Asymmetric addition of in situ generated chiral α-fluoro-γ-sulfinylbenzyl carbanion towards aromatic (II) and aliphatic aldehydes (VI) proceeds with complete control of facial selectivity at the carbanion and with moderate to high anti-diastereoselectivity to afford the product fluorohydrins in up to 92% d.e. Desulfinylation is readily achieved using tBuLi. Additionally, a one-pot monofluoroalkylation—desulfinylation—oxida- tion sequence is carried out to afford chiral α-fluoroketones (V). The asymmetric monofluoroalkylation is also successfully applied to ketones (X). — (ARROYO, Y.; SANZ-TEJEDOR*, M. A.; PARRA, A.; GARCIA RUANO, J. L.; Chem. Eur. J. 18 (2012) 17, 5314-5318, http://dx.doi.org/10.1002/chem.201103919 ; Dep. Quim. Org., Fac. Cienc., Univ. Valladolid, E-47011 Valladolid, Spain; Eng.) — Mischke 36- 055
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Transcript of ChemInform Abstract: Asymmetric Nucleophilic Monofluorobenzylation of Carbonyl Compounds: Synthesis...
AlcoholsQ 0230 DOI: 10.1002/chin.201236055
Asymmetric Nucleophilic Monofluorobenzylation of Carbonyl Compounds: Synthesis of Enantiopure vic-Fluorohydrins and α-Fluorobenzylketones. — Asymmetric addition of in situ generated chiral α-fluoro-γ-sulfinylbenzyl carbanion towards aromatic (II) and aliphatic aldehydes (VI) proceeds with complete control of facial selectivity at the carbanion and with moderate to high anti-diastereoselectivity to afford the product fluorohydrins in up to 92% d.e. Desulfinylation is readily achieved using tBuLi. Additionally, a one-pot monofluoroalkylation—desulfinylation—oxida-tion sequence is carried out to afford chiral α-fluoroketones (V). The asymmetric monofluoroalkylation is also successfully applied to ketones (X). — (ARROYO, Y.; SANZ-TEJEDOR*, M. A.; PARRA, A.; GARCIA RUANO, J. L.; Chem. Eur. J. 18 (2012) 17, 5314-5318, http://dx.doi.org/10.1002/chem.201103919 ; Dep. Quim. Org., Fac. Cienc., Univ. Valladolid, E-47011 Valladolid, Spain; Eng.) — Mischke
36- 055
ChemInform 2012, 43, issue 01 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ChemInform 2012, 43, issue 01 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
