An efficient protocol for the stereoselective dihydroxylation of ene-ester systems
An efficient protocol for the stereoselective dihydroxylation of ene-ester systems
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DOI：
10.1016/s0040-4020(98)00800-x
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发表时间：
1998-10-22
期刊：
影响因子：
2.1
通讯作者：
Roberts, SM
中科院分区：
文献类型：
--
作者：
Hermitage, SA;Murphy, A;Roberts, SM
利用α-甲基-β-OTBS体系固有的非对映选择性，在经典的OsO 4和NMO催化条件下，实现了烯酯体系的双羟基化反应，获得了良好的产率和非对映选择性.这种固有的非对映体选择可以使用“超级”AD混合物逆转，以同样良好的选择性得到相反的非对映体。使用改性的“超级”AD混合物在二烯酯中进行二羟基化的区域选择性差。该方法可用于海洋大环内酯Altohyrtin A部分结构的合成。(C)1998爱思唯尔科技有限公司版权所有。
Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation 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. (C) 1998 Elsevier Science Ltd. All rights reserved.