The asymmetric hydrogenation of 2-phenethylacrylic acid as the key step for the enantioselective synthesis of Citralis Nitrile®

Scrivanti, Alberto; Bovo, S; Ciappa, A; Matteoli, Ugo

doi:10.1016/j.tetlet.2006.10.129

Cited by 34 publications

(13 citation statements)

References 24 publications

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“…2, the higher the temperature, the higher the enantioselectivity. This unusual behavior has been previously reported [24d] [26], but the relevant mechanistic aspects have not yet been investigated.…”

supporting

confidence: 66%

“…We have developed an alternative approach to non-racemic Citralis Nitrile (Scheme 6) [26], the key step of which consists in the asymmetric hydrogenation of 2-(2-phenylethylprop-2-enoic acid (17). The latter was prepared by carbonylation of (but-3-ynyl)benzene (16) in the presence of a catalyst system formed by combining Pd(OAc) 2 with diphenyl(pyridin-2-yl)phosphine and MsOH.…”

Section: Citralismentioning

confidence: 99%

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Homogeneous Asymmetric Catalysis in Fragrance Chemistry

Ciappa

Bovo

Bertoldini

et al. 2008

Chemistry & Biodiversity

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Opposite enantiomers of a chiral fragrance may exhibit different olfactory activities making a synthesis in high enantiomeric purity commercially and scientifically interesting. Accordingly, the asymmetric synthesis of four chiral odorants, Fixolide, Phenoxanol, Citralis, and Citralis Nitrile, has been investigated with the aim to develop practically feasible processes. In the devised synthetic schemes, the key step that leads to the formation of the stereogenic center is the homogeneous asymmetric hydrogenation of a prochiral olefin. By an appropriate choice of the catalyst and the reaction conditions, Phenoxanol, Citralis, and Citralis Nitrile were obtained in high enantiomeric purity, and odor profiles of the single enantiomers were determined.

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supporting

confidence: 66%

Section: Citralismentioning

confidence: 99%

Homogeneous Asymmetric Catalysis in Fragrance Chemistry

Ciappa

Bovo

Bertoldini

et al. 2008

Chemistry & Biodiversity

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“…By comparing the optical rotation value {[α

+2.67 (c 0.15, MeOH)} of 2 with ( S )-2-methyl-3-phenylpropionic acid {[α

+26.3 (c 1.0, CHCl 3 )} and ( R )-2-methyl-3-phenylpropionic acid {[α

−18 (c 1.0, CHCl 3 )} [ 9 ], the absolute configuration of 2 was proposed to be S . Other examples related to the optical rotation values included ( R )-2-methyl-4-phenylbutanoic acid ([α

−28.0) [ 10 ] as well as 2( S )-methylbutyric acid ([α] D +19) and 2( R )-methylbutyric acid ([α] D −19) [ 11 ]. Therefore, the structure of 2 was elucidated as ( S )-3-(3-carboxybutyl)-4-methoxybenzoic acid, which was named as rhizopycnis acid B.…”

Section: Resultsmentioning

confidence: 99%

Two New Anisic Acid Derivatives from Endophytic Fungus Rhizopycnis vagum Nitaf22 and Their Antibacterial Activity

Wang¹,

Li²,

Zhang³

et al. 2018

Molecules

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Rhizopycnis acids A (1) and B (2), two new anisic acid derivatives, were obtained from the ethyl acetate extract of the fermentation cultures of Rhizopycnis vagum, an endophytic fungus isolated from the healthy tissues of Nicotiana tabacum. The structures of the two compounds were determined through a series of 1D and 2D NMR and HRMS spectral analyses. Both compounds were the first anisic acid derivatives containing methylbutanoic/methylbutenoic acid group found in fungi. 1 and 2 displayed antibacterial activity against six tested bacteria with IC50 values in the range 16.1~81.3 μg/mL.

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“…Brown et al found deuterium was incorporated onto the C 1-3 positions, and only two deuterium atoms, on average, were incorporated into each molecule. This is indicative of double bond migration concurrent with the hydrogenation event.…”

Section: Carboxylate Estersmentioning

confidence: 99%

Comparison of Asymmetric Hydrogenations of Unsaturated Carboxylic Acids and Esters

Khumsubdee

Burgess

2013

ACS Catal.

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As methodology development matures it can be difficult to discern the most effective ways of performing certain transformations from the rest. This review summarizes the most important contributions leading to asymmetric hydrogenations of simple unsaturated-acid and ester substrates, with the objective of highlighting at least the best types of catalysts for each. Achievements in the area are described and these reveal situations where further efforts should be worthwhile, and ones where more research is only likely to give diminishing returns. In general, our conclusions are that the most useful types of catalysts for unsaturated-acids and -esters tend to be somewhat different, simple substrates have been studied extensively, and the field is poised to address more complex reactions. These could be ones involving alternative, particularly cyclic, structures, chemoselectivity issues, and more complex substrate stereochemistries.

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The asymmetric hydrogenation of 2-phenethylacrylic acid as the key step for the enantioselective synthesis of Citralis Nitrile®

Cited by 34 publications

References 24 publications

Homogeneous Asymmetric Catalysis in Fragrance Chemistry

Homogeneous Asymmetric Catalysis in Fragrance Chemistry

Two New Anisic Acid Derivatives from Endophytic Fungus Rhizopycnis vagum Nitaf22 and Their Antibacterial Activity

Comparison of Asymmetric Hydrogenations of Unsaturated Carboxylic Acids and Esters

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