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ChemInform Abstract: Desymmetrization of meso-1,2-Diols via Chiral Oxazaborolidine-Mediated Ring-Cleavage of Acetal Derivatives with Silyl Ketene S,O-Acetal.

✍ Scribed by M. KINUGASA; T. HARADA; A. OKU

Publisher
John Wiley and Sons
Year
2010
Weight
41 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Desymmetrization of meso-1,2-Diols via Chiral Oxazaborolidine-Mediated Ring-Cleavage of Acetal Derivatives with Silyl Ketene S,O-Acetal.

-The desymmetrization of a variety of meso-1,2-diols is readily achieved by chiral oxazaborolidine-mediated enantioselective ring cleavage of acetals of type syn-(III). Since anti-(III) are unreactive, purification of the starting material is not necessary. Moreover, mixtures of dl/meso substrates (I) can be used to give exclusively the desired product [cf. (Va)]. Products (V) and (VII) are suitable building blocks in asymmetric synthesis as is demonstrated by the preparation of both enantiomers of amino alcohol (XII).

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