Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis

Scrivanti, Alberto; Bertoldini, Matteo; Beghetto, Valentina; Matteoli, Ugo

doi:10.1016/j.tet.2007.11.019

Cited by 10 publications

(16 citation statements)

References 51 publications

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“…The reduction product of p-tert-butylcinnamaldehyde (1b, Scheme 1) is the olfactory principle of the lily-of-the-valley 2c, 12 and is marketed under the trade name Lilial TM or Lysmeral TM , whereas the m,p-methylenedioxy aldehyde (2b) is the active ingredient of various perfumes and is marketed as Helional TM or Tropional TM . 1,13 Scheme 1 Asymmetric bioreduction of a-methylcinnamaldehyde derivatives 1a-3a.…”

Section: Resultsmentioning

confidence: 99%

Bioreduction of α-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial™ and Helional™

et al. 2010

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Nonracemic aryl-substituted alpha-methyldihydrocinnamaldehyde derivatives employed as olfactory principles in perfumes (Lilial, Helional) were obtained via enzymatic reduction of the corresponding cinnamaldehyde precursors using cloned and overexpressed ene-reductases. (R)-Enantiomers were obtained using the old-yellow-enzyme (OYE) homolog YqjM from Bacillus subtilis and 12-oxophytodienoic acid reductase isoenzyme OPR1 from tomato (e.e.(max) 53%), and (S)-aldehydes were furnished in up to 97% e.e. using isoenzyme OPR3, nicotinamide 2-cyclohexene-1-one reductase NCR from Zymomonas mobilis and yeast OYE isoenzymes 1-3 under optimised reaction conditions in the presence of t-butyl methyl ether as the co-solvent. The stereochemical outcome of the reduction of alpha-methylcinnamaldehyde using NCR and OYEs 1-3 [previously reported to be (R)] was unambiguously corrected to be (S).

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Section: Resultsmentioning

confidence: 99%

Bioreduction of α-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial™ and Helional™

et al. 2010

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“…Phosphine ligands are extremely common in palladium catalysis, and several of them have led to catalysts loadings of 100 mol ppm or less. Tri( tert ‐butyl)phosphine, the tetraphosphine Tedicyp [ cis‐cis‐cis ‐1,2,3,4‐tetrakis(diphenylphosphinomethyl)cyclopentane], and a ferrocenyl triphosphine gave few examples of Heck reaction using 100 or 50 mol ppm. By using the tetradentate phosphine ligand Tedicyp, Santelli and co‐workers were able to react hex‐1‐en‐3‐ol or oct‐1‐en‐3‐ol with various aryl bromides at a catalyst loading of 100 to 20 mol ppm .…”

Section: Mizoroki–heck Couplingmentioning

confidence: 99%

Recent Advances in Palladium‐Catalyzed Cross‐Coupling Reactions at ppm to ppb Molar Catalyst Loadings

2017

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We review here new developments in decreasing the catalyst loadings in palladium-catalyzed C-C bond-formation reactions to mol ppm or mol ppb levels.T his decreasest he cost of the catalyst and the toxicity of the reactions ystem, making the reactionm ore attractive to industry.T he Heck reaction, Sonogashira reaction, Suzuki-Miyaurac rosscoupling reaction, other cross-coupling reactions,a nd allylic arylation reactions are separately discussedt o show clearly the progress made in each type of reaction. Apart from the catalyst loading, the other parameters of the reaction( temperature,s olvent, etc.) are brieflyd iscussed to illustrate the shift toward greenerc onditions.F or most reactions,t his shift is underway or wella dvanced, andc atalyst loadings have been decreasedt ob elow 1mol ppm. An abundance of catalytic systems are now available,a nd it is sometimes difficult to identify the best one,b ecause the substratese xamined can vary widely from publication to publication.I nt he future,e mphasis should be placed on the studyingt he full scope of the reaction at mol ppm catalyst loadings,r athert han examining af ew examples at these levels during the reaction-optimization process.1I ntroduction 2M izoroki-Heck Coupling 3S onogashira Coupling 4S uzuki-MiyauraCross-Coupling 5O ther Cross-Coupling Reactions 6A llylic Arylation 7C onclusions

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“…PtBu 3 was introduced to Pd-mediated cross coupling chemistry in 1987 by Nicholas in the amidation of vinyl chloride. 82 In various coupling reactions such as Suzuki-Miyaura, 55,83,84 Heck-Mizoroki, [85][86][87][88][89] Sonogashira, [90][91][92] Buchwald-Hartwig amination, 11,[93][94][95][96] Negishi, [97][98][99][100] Hiyama, 101 Stille, 102,103 Kumada, 104 a-arylation, 105-107 silylation, 108 and cyanation, 109 the palladium complexes of PtBu 3 demonstrated their excellent performance.…”

Section: Tri-tert-butylphosphine Ptbumentioning

confidence: 99%

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

2010

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The strong electron-donation and the steric bulk of trialkylphosphines renders them as very useful ligands for palladium-catalyzed cross coupling reactions. This critical review reports on the synthesis of two families of trialkylphosphines (diadamantylalkylphosphines, fluorenyldialkylphosphines) and the properties of the respective palladium complexes in various cross coupling reactions, which evolved as alternatives to the classical Pd/PtBu(3) system. In contrast to the latter phosphine the new classes of ligands are characterized by a highly flexible ligand design, which allows the fine tuning of catalytic properties to the specific needs of certain substrates and also enables the attachment of additional tags to impart certain useful properties onto the respective phosphines (179 references).

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Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis

Cited by 10 publications

References 51 publications

Bioreduction of α-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial™ and Helional™

Bioreduction of α-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial™ and Helional™

Recent Advances in Palladium‐Catalyzed Cross‐Coupling Reactions at ppm to ppb Molar Catalyst Loadings

Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3

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