4.6 Article

Dramatic effect of modified boranes in diastereoselective reduction of chiral cyclic α-ketophosphinates

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RSC ADVANCES
卷 2, 期 3, 页码 816-818

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ra00799a

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  1. ANR Emergence Bio [IDEPHOST 2009-2011]

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Phostines have been recently described as compounds having antiproliferative properties. Original synthesis of this new class of phosphinic analogs of pyranoses led to a mixture of four diastereomers 3-6 with unequal bioactivities. The most active compound 4 was originally obtained from a mixture of these four diastereomers by selective precipitation, giving firstly two diastereomers 3 and 4, epimers at the carbon atom. From the latter mixture 3 and 4, oxidation with Dess-Martin reagent afforded corresponding alpha-ketophosphinate 7, which by diastereoselective reduction using a chiral agent based on sodium borohydride and L-proline, gave preferentially the active diastereomer 4. In addition, use of a multivalent cation also increased the diastereoselectivity favourably.

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