Dihydroxylation of polyenes using Narasaka's modification of the Upjohn procedure
Dihydroxylation of polyenes using Narasaka's modification of the Upjohn procedure
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DOI：
10.1021/jo980850l
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发表时间：
1998-10-16
影响因子：
3.6
通讯作者：
Sharpless, KB
中科院分区：
文献类型：
--
作者：
Gypser, A;Michel, D;Sharpless, KB
用苯硼酸、n -甲基啉n -氧化物（NMO）和四氧化二锇在无水溶剂中研究了多种市售多烯的二羟基化反应。在某些情况下，多重氧化步骤的非对映选择性受到中间烯二醇作为苯硼酯的原位保护的影响，从而提供了标准厄普约翰二羟基化程序无法获得的多元醇。还描述了苯硼酯的一种方便的氧化脱保护。
Dihydroxylation of a variety of commercially available polyenes has been investigated using phenylboronic acid, N-methylmorpholine N-oxide (NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectivity of multiple oxidation steps is in some cases affected by the in situ protection of the intermediate ene-diols as phenyboronic esters, affording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic esters is also described.