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An efficient protocol for the stereoselective dihydroxylation of ene-ester systems

✍ Scribed by Stephen A. Hermitage; Alison Murphy; Poul Nielsen; Stanley M. Roberts

Book ID
104208870
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
915 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO( and NMO conditions using the intrinsic diastereoselectivity in a-methyl ~-OTBS systems. This inlxinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The reginselection of dthydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A.

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