Process for enzymatic acylation of alcohols with alkoxyvinyl ace

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...

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435128, 435134, 435135, 435155, 435158, 435198, 435280, 435874, 435922, C12N 920, C12P 4100, C12P 762

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057563217

ABSTRACT:
Methods for the enzyme catalyzed acylation of primary and secondary alcohols using an enol ester as the acyl donor are described. The acylation occurs in organic media, and is enantioselective for racemic or prochiral alcohols. The reaction is irreversible, and produces unreactive by-products.

REFERENCES:
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Y. Kita et al., "Novel Efficient Synthesis of 1-Ethoxyvinyl Esters Using Ruthenium Catalysts and their Use in Acylation of Amines and Alcohols: Synthese of Hydrophilic 3'-N-Acylated Oxaunomycin Derivatives", J. Chem. Soc. Perkin Trans. 1: 2999-30005 (1993).
Y. Kita et al., "A Novel Efficient Synthesis of 1-Ethoxyvinyl Esters and Thei Use in Acylation of Amines and Alcohols: Synthesis of Water-Soluble Oxaunomycin Derivatives", SYNLETT pp. 273-274 (1993).
J. Arens, "The Chemistry of Acetylenic Ethers XIII. Acetylenic ethers as reagents for the preparation of amides", Recueil Chem. Pays Bas. 74: 769-770 (1955).
Z. Kabouche et al., "Enol Esters as Intermediates for the Facile Conversion of Amino Acids into Amides and Dipeptides", Tetrahedron Letters 32(39): 5359-5362 (1991).
Kita et al. Tetrahedron Letters vol. 37 No. 41 pp. 7369-7372, 7 Oct. 1996.

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