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Original scientific paper

Preparation of Chiral Diphenylphosphines from D-Glucose and Enantioselective Hydrogenation with Their Rh(l) Complexes

Ivan Habuš ; Rudjer Bošković Institute, Department of Organic Chemistry and Biochemistry, P.O.B. 1016, 41001 Zagreb, Yugoslavia
ZLata Raza ; Rudjer Bošković Institute, Department of Organic Chemistry and Biochemistry, P.O.B. 1016, 41001 Zagreb, Yugoslavia
Vitomir Šunjić ; Rudjer Bošković Institute, Department of Organic Chemistry and Biochemistry, P.O.B. 1016, 41001 Zagreb, Yugoslavia


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Abstract

(2R,3S)-2-Methylsulfonyloxymeihyl-3-methylsulfonyloxy-tetrahydropyran (4), derived from n-glucose, is diphenylphosphinated to (2R,3R)-2-diphenylphosphinomethyl-3-diphenylphosphino-tetrahydropyran (7), which is formed as aminor product. Compound 8 is the predominant product, formed on 3,4-elimination. Preparation
and characterization of the rhodium(I) complexes 10-12 is described.
Complex 10 of bidentate Iigand 7 exhibits in hydrogenation of Z-a-N-acetylaminocinnamic acid enantioselectivity comparable to that obtained with rhodium(I) complex of (-)-DIOP (-70010e. e.). Saturated monophosphine, (2S)-2-diphenylphosphinomethyl-tetrahydropyran (9) affords mixed rhodium(I) complex (11, 12), which exhibits low enantioselectivity.

Keywords

Hrčak ID:

176017

URI

https://hrcak.srce.hr/176017

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