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On the Origin of the Facial Selectivity of the Sharpless Asymmetric Dihydroxylation of Styrene Derivatives.

✍ Scribed by Nicolas Moitessier; Christophe Henry; Christophe Len; Denis Postel; Yves Chapleur


Publisher
John Wiley and Sons
Year
2003
Weight
159 KB
Volume
34
Category
Article
ISSN
0931-7597

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✦ Synopsis


Abstract

For Abstract see ChemInform Abstract in Full Text.


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The catalytic asymmetric dihydroxylation of several allyl 2-O-benzyl-Ξ±-D-xylosides with AD-mix Ξ² and PYR(DHQD) 2 shows almost no diastereofacial selectivity if the 3-and 4-OH groups are unprotected or acetylated. Acetal, benzyl ethers and benzoyl esters enhance the diastereoselectivity, in the oppos