- Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification
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We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.
- Hofmann, Christine,Schümann, Jan M.,Schreiner, Peter R.
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p. 1972 - 1978
(2015/02/19)
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- Copper ion-induced activation and asymmetric benzoylation of 1,2-diols: Kinetic chiral molecular recognition
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New catalytic ability of copper(II) ion has been exploited for monobenzoylation of 1,2-diols. The catalyst can be readily modified by ligation to acquire higher stereoselectivity. Highly effective kinetic resolution of dl-1,2-diols was achieved. The enant
- Matsumura, Yoshihiro,Maki, Toshihide,Murakami, Sachie,Onomura, Osamu
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p. 2052 - 2053
(2007/10/03)
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- Desymmetrization of meso-hydrobenzoin via stereoselective enzymatic esterification
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Desymmetrization of meso-hydrobenzion by irreversible acyl transfer using vinyl acetate as the acyl donor in the presence of Rhizopus javanicus lipase or Candida cylindracea lipase enables the preparation of (R)-1-acetoxy-(S)- 2-hydroxy-1,2-diphenylethane and (S)-1-acetoxy-(R)-2-hydroxy-1,2- diphenylethane respectively in excellent optical purity.
- Nicolosi,Patti,Piattelli,Sanfilippo
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p. 283 - 288
(2007/10/02)
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- OXIDATION BY COBALT(III) ACETATE. PART 6. A NOVEL SYNTHESIS OF THE GLYCOL MONOACETATES FROM AROMATIC OLEFINS IN WET ACETIC ACID
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Oxidation of various aryl-conjugated olefins with cobalt(III) acetate in wet acetic acid under nitrogen affords the glycol monoacetates in moderate to good yields.None of the phenyl rearrangement product is formed in the present reactions.These results are best interpreted by assuming the formation of a Co-co-ordinated intermediate.
- Hirano, Masao,Morimoto, Takashi
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p. 1033 - 1036
(2007/10/02)
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- Oxidation of Styrene Derivatives by S2O82--CuII in Acetic Acid and Acetonitrile. Reaction Paths in Oxidations via Radical Cations
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β-Aryl carbonyl compounds are major products in the oxidation of a variety of styrene derivatives by S2O82--CuII.Evidence is presented that they arise via oxidation to a radical cation, nucleophilic addition of water to give a β-hydroxyalkyl radical, CuII oxidation to epoxide, and finally acid-catalyzed rearrangement.Data on oxidation of alkyl aromatics with additional functional groups are presented.With ether and amino groups, oxidation occurs at the functional group even when it is remote from the aryl nucleus.These and previous data are summarized to give a coherent picture of the various paths by which aryl side chains may be degraded via initial radical cation intermediates.
- Walling, Cheves,El-Taliawi, Gamil M.,Amarnath, Kalyani
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p. 7573 - 7578
(2007/10/02)
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