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Phosphinites of carbohydrates as chiral ligands for asymmetric synthesis catalyzed by complexes, I. Hydrogenation of aminoacid precursors by rhodium(I) chelates of methyl 4,6-O-benzylidente-2,3-bis-O-(diphenylphosphino)-α-D-glucopyranosides

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Abstract

A simple method for preparing carbohydrate-bis-phosphinites of methyl α-D-glucopyranosides of glucose and galactose protected by benzylidene groups in 4,6-position leads to chelating ligands which are useful in the asymmetric hydrogenation of prochiral aminoacid precursors catalyzed by rhodium(I), producing optical yields up to 75%. Cationic complexes are particularly active.

Abstract

Простым синтезом бис фосфинитов углеводов как метил-а-D-глюкопиранозиды глюкозы и галактозы замещенные в 4,6-позиции с бензилиден-группой получаются хелатные лиганды используемые в присутствии родия (I) в каталитическом гидрировании прохиральных предшественников аминокислот с оптическим выходом до 75%. Особенно активными являютоя катионные комплексы.

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Authors and Affiliations

  1. Department of Complex Catalysis, Central Institute of Organic Chemistry, Rostock, GDR

    R. Selke

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  1. R. Selke
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Selke, R. Phosphinites of carbohydrates as chiral ligands for asymmetric synthesis catalyzed by complexes, I. Hydrogenation of aminoacid precursors by rhodium(I) chelates of methyl 4,6-O-benzylidente-2,3-bis-O-(diphenylphosphino)-α-D-glucopyranosides. React Kinet Catal Lett 10, 135–138 (1979). https://doi.org/10.1007/BF02075980

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  • DOI: https://doi.org/10.1007/BF02075980

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