Dihydroxylation of polyenes using Narasaka's modification of the Upjohn procedure

被引：32

作者：

Gypser, A

Michel, D

Nirschl, DS

Sharpless, KB

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 21期

关键词：

D O I：

10.1021/jo980850l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：7322 / 7327

页数：6

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