- Cross β-alkylation of primary alcohols catalysed by DMF-stabilized iridium nanoparticles
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A simple method for the cross β-alkylation of linear alcohols with benzyl alcohols in the presence of DMF-stabilized iridium nanoparticles was developed. The nanoparticles were prepared in one-step and thoroughly characterized. Furthermore, the optimum reaction conditions have a wide substrate scope and excellent product selectivity.
- Kobayashi, Masaki,Yamaguchi, Hiroki,Suzuki, Takeyuki,Obora, Yasushi
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supporting information
p. 1950 - 1954
(2021/03/16)
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- Cross β-arylmethylation of alcohols catalysed by recyclable Ti-Pd alloys not requiring pre-activation
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Ti-Pd alloy catalysts were developed for the cross β-arylmethylation between arylmethylalcohols and different primary alcohols via a hydrogen autotransfer mechanism. The alloy catalysts could be reused multiple times without the need for pre-activation. Analysis of the reaction solution by inductively coupled plasma atomic absorption spectroscopy indicated that only a minimal amount of Ti and no Pd was leached from the catalyst.
- Utsunomiya, Masayoshi,Kondo, Ryota,Oshima, Toshinori,Safumi, Masatoshi,Suzuki, Takeyuki,Obora, Yasushi
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supporting information
p. 5139 - 5142
(2021/05/31)
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- Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation
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Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process invol
- Emmetiere, Fabien,Grenning, Alexander J.
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p. 3077 - 3085
(2020/08/10)
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- Ru-Catalyzed Cross-Dehydrogenative Coupling between Primary Alcohols to Guerbet Alcohol Derivatives: With Relevance for Fragrance Synthesis
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A simple method has been developed for the cross dehydrogenative coupling between two different primary alcohols using readily available RuCl2(PPh3)3 as a precatalyst through the borrowing-hydrogen approach. The present methodology is applicable to a large variety of alcohol derivatives including long chain aliphatic alcohols and heteroaryl alcohols. In addition, the methodology was applied in a straightforward protocol to synthesize commercially available fragrances such as Rosaphen and Cyclamenaldehyde in good yields.
- Manojveer, Seetharaman,Salahi, Saleh,Wendt, Ola F.,Johnson, Magnus T.
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p. 10864 - 10870
(2018/09/06)
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- SuperQuat, (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one for the asymmetric synthesis of α-substituted-aldehydes
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Reduction of α-substituted-(S)-N-acyl-4-benzyl-5,5-dimethyl-oxazolidin-2-ones with DIBAL-H in CH2Cl2 affords α-substituted aldehydes with no loss of stereochemical integrity at their α-centre. Copyright (C) 2000 Elsevier Science Ltd.
- Bull, Steven D.,Davies, Stephen G.,Nicholson, Rebecca L.,Sanganee, Hitesh J.,Smith, Andrew D.
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p. 3475 - 3479
(2007/10/03)
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- 2-substituted-(2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1- yl)glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 1. Effects of alkyl, arylalkyl, and diarylalkyl substitution
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In this paper, we describe the synthesis of a series of α-substituted analogues of the potent and selective group II metabotropic glutamate receptor (mGluR) agonist (1S,1'S,2'S)-carboxy-cyclopropylglycine (2, L-CCG 1). Incorporation of a substituent on the amino acid carbon converted the agonist 2 into an antagonist. All of the compounds were prepared and tested as a aeries of four isomers, i.e., two racemic diastereomers. We explored alkyl substitution, both normal and terminally branched; phenylalkyl and diphenylalkyl substitution; and a variety of aromatic and carbocyclic surrogates for phenyl. Affinity for group II mGluRs was measured using [3H]glutamic acid (Glu) binding in rat forebrain membranes. Antagonist activity was confirmed for these compounds by measuring their ability to antagonize (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid-induced inhibition of forskolin-stimulated cyclic-AMP in RGT cells transfected with human mGluR2 and mGluR3. We found that while alkyl substitution provided no increase in affinity relative to 2, phenylethyl and diphenylethyl substitution, as in 105 and 109, respectively, were quite beneficial. The affinity of 109 was further enhanced when the two aromatic rings were joined by an oxygen or sulfur atom to form the tricyclic xanthylmethyl and thioxanthylmethyl amino acids 113 and 114, respectively. Amino acid 113, with an IC50 of 0.010 μM in the [3H]Glu binding assay, was 52-fold more potent than 2, whose IC50 was 0.47 μM.
- Ornstein, Paul L.,Bleisch, Thomas J.,Arnold, M. Brian,Wright, Rebecca A.,Johnson, Bryan G.,Schoepp, Darryle D.
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p. 346 - 357
(2007/10/03)
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