Regiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation

Secondary allylic alcohols were synthesized from linear allylic halides or carbonates using a catalytic amount of a ruthenium complex in the presence of boronic acid. The effects of solvent, base, ruthenium precursor, and boronic acid were fully explored, and the scope of the reaction was extended to various substrates. We also describe a preliminary investigation towards an enantioselective process.

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“…1-Phenylprop-2-en-1-ol: [42] 1-(4-Nitrophenyl)prop-2-en-1-ol: 1-(Naphthalen-1-yl)prop-2-en-1-ol: [43] …”

Section: Methodsmentioning

confidence: 99%

Ruthenium‐Catalyzed Synthesis of Allylic Alcohols: Boronic Acid as a Hydroxide Source

Bouziane

Hélou

Carboni

et al. 2008

Chemistry A European J

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“…[11,27,28] Racemic substrates S1-S7 were prepared as previously reported. [29,30,31,32] [Pd(h [33] [Pd(h [34] and [35] were prepared as previously described. …”

Section: Experimental Section General Considerationsmentioning

confidence: 99%

Pyranoside Phosphite‐Oxazoline Ligand Library: Highly Efficient Modular P,N Ligands for Palladium‐Catalyzed Allylic Substitution Reactions. A Study of the Key Palladium Allyl Intermediates

Mata¹,

Pàmies²,

Diéguez³

2009

Adv Synth Catal

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Abstract:We have screened a library of modular phosphite-oxazoline ligands for asymmetric allylic substitution reactions. The library is efficiently prepared from the commercially available and cheap dglucosamine. The introduction of a phosphite moiety into the ligand design is highly advantageous for the product outcome. Therefore, this ligand library affords good-to-excellent reaction rates [TOFs up to 600 mol substrate (mol Pd h) À1] and enantioselectivities (ees up to 99%) and, at the same time, shows a broad scope for mono-, di-and trisubstituted linear hindered and unhindered substrates and cyclic substrates. The NMR studies on the palladium allyl intermediates provide a deeper understanding about the effect of the ligand parameters on the origin of enantioselectivity.

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“…Allylic carbonates and acetates were synthesized by using known experimental procedures. [29] All chiral primary amines were obtained from BASF. Chiral secondary amines 18-23 were prepared according to the procedure described previously.…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

Phosphoramidite Ligands in Iridium‐Catalyzed Allylic Substitution

Polet

Alexakis

Tissot-Croset

et al. 2006

Chemistry A European J

181

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A new phosphoramidite ligand was used in the iridium-catalyzed allylic substitution reaction. This permitted high regio- and enantioselectivities on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resolution reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics was explored in detail, as was the role of the substituent in the ortho-position of the amine moiety.

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Regiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation

Cited by 121 publications

References 23 publications

Ruthenium‐Catalyzed Synthesis of Allylic Alcohols: Boronic Acid as a Hydroxide Source

Ruthenium‐Catalyzed Synthesis of Allylic Alcohols: Boronic Acid as a Hydroxide Source

Pyranoside Phosphite‐Oxazoline Ligand Library: Highly Efficient Modular P,N Ligands for Palladium‐Catalyzed Allylic Substitution Reactions. A Study of the Key Palladium Allyl Intermediates

Phosphoramidite Ligands in Iridium‐Catalyzed Allylic Substitution

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