- Hydration of Olefins with Molecular Oxygen and Triethylsilane Catalyzed by Bis(trifluoroacetylacetonato)cobalt(II)
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In the presence of a catalytic amount of bis(trifluoroacetylacetonato)cobalt(II), various olefins react smoothly with molecular oxygen (oxidant) and triethylsilane (reductant) to afford the corresponding alcohols regioselectively in good yields along with ketones.
- Isayama, Shigeru,Mukaiyama, Teruaki
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- Simple and practical method for selective acylation of primary hydroxy group catalyzed by N-methyl-2-phenylimidazole (Ph-NMI) or 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT)
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N-Methyl-2-phenylimidazole (Ph-NMI) and 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT) catalyzed selective acylation of primary alcohols using acid anhydrides. The Ph-NMI- or Ph-IBT-catalyzed reaction using (PhCO)2O as an acylating agent could particularly acylate the primary hydroxy group of 1,n-diols (n ≥ 3) with a high, synthetically useful selectivity.
- Ibe, Kouta,Hasegawa, Yu-Suke,Shibuno, Misuzu,Shishido, Tsukasa,Sakai, Yuzo,Kosaki, Yu,Susa, Keisuke,Okamoto, Sentaro
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p. 7039 - 7042
(2015/01/08)
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- Chemoselective reduction of aldehydes over ketones with sodium tris(hexafluoroisopropoxy)borohydride
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Chemoselective reduction of aldehydes in the presence of ketones was achieved using sodium tris(hexafluoroisopropoxy)borohydride which can be stored as a THF solution. Georg Thieme Verlag Stuttgart.
- Kuroiwa, Yasutaka,Matsumura, Shuichi,Toshima, Kazunobu
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p. 2523 - 2525
(2009/04/16)
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- Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis
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Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary ones as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under the present reaction conditions. This method is highly practical since operation is quite simple. Esters and solvents can be used without purification and no inert atmosphere is necessary. The products can be isolated simply by column chromatography or distillation without aqueous workup.
- Orita, Akihiro,Sakamoto, Katsumasa,Hamada, Yuji,Mitsutome, Akihiro,Otera, Junzo
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p. 2899 - 2910
(2007/10/03)
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- Organotin-Mediated Monoacylation of Diols with Reversed Chemoselectivity: A Convenient Synthetic Method
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The organotin-mediated monoesterification of unsymmetrical diols with reversed chemoselectivity has been explored to ascertain scope and limits of the method and to provide an easy and convenient synthetic procedure.The reaction has been performed on a set of substituted diols with some acylating agents usually employed as protecting groups.Two different procedures have been devised to obtain either the desired diol monoesters directly or the corresponding trialkylsilyl ethers as protected derivatives.The latter provides a convenient approach to the preparation of easily interconvertible diol monoesters.Also, the reaction has been optimized as a one-pot procedure, avoiding the isolation and purification of the stannylated intermediates.The reversed monoesterification method has been successfully applied to 1,2-, 1,3-, and 1,4-diols of primary-secondary, primary-tertiary, and secondary-tertiary types and to ether functions containing 1,2-diols.Within its limits, the described method represents the first direct one-pot monoesterification of diols at the most substituted site, allowing some remarkable achievements as (a) an almost regiospecific reversed monobenzoylation of some 1,2-diols, (b) the selective acylation of the tertiary hydroxyl of a primary-tertiary diol, and (c) a highly selective preparation of secondary pivalate of primary-secondary diols.
- Reginato, Gianna,Ricci, Alfredo,Roelens, Stefano,Scapecchi, Serena
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p. 5132 - 5139
(2007/10/02)
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- A New Method for Preparation of Alcohols from Olefins with Molecular Oxygen and Phenylsilane by the Use of Bis(acetylacetonato)cobalt(II)
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In the presence of a catalytic amount of bis(acetylacetonato)cobalt(II), various olefins react smoothly with molecular oxygen and phenylsilane at room temperature to afford the corresponding alcohols in good yields under neutral conditions.
- Isayama, Shigeru,Mukaiyama, Teruaki
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p. 1071 - 1074
(2007/10/02)
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- BIS(TRIFLUOROACETYLACETONATO)COBALT(II) CATALYZED OXIDATION-REDUCTION HYDRATION OF OLEFINS SELECTIVE FORMATION OF ALCOHOLS FROM OLEFINS
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Various olefins are hydrated with molecular oxygen (oxidant) and a secondary alcohol (reductant) in the presence of a catalytic amount of bis(trifluoroacetylacetonato)cobalt(II) in good yields
- Inoki, Satoshi,Kato, Koji,Takai, Toshihiro,Isayama, Shigeru,Yamada, Tohru,Mukaiyama, Teruaki
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p. 515 - 518
(2007/10/02)
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- 3-ACYL-2-OXAZOLONE-ZIRCONIUM COMPLEXES AS EXCELLENT REAGENTS FOR HIGHLY REGIOSELECTIVE ACYLATION OF POLYALCOHOLS
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In combination with 3-acyl-2-oxazolones, zirconium complexes such as zirconium acetylacetonate and zirconocene chloride hydride-Mg serve well as effective catalysts for regioselective acylation of polyalcohols including 1,2-diols to permit higly preferential protection of primary hydroxyl groups.
- Kunieda, Takehisa,Mori, Takashi,Higuchi, Tsunehiko,Hirobe, Masaaki
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p. 1977 - 1980
(2007/10/02)
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