Selective dihydroxylation of non-conjugated dienes in favor of the terminal olefin
Selective dihydroxylation of non-conjugated dienes in favor of the terminal olefin
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DOI：
10.1016/s0040-4039(97)00861-7
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发表时间：
1997-06-09
影响因子：
1.8
通讯作者：
Sclafani, JA
中科院分区：
文献类型：
--
作者：
Andrus, MB;Lepore, SD;Sclafani, JA
使用市售的四氧化锇 AD-mix-α 试剂对非共轭二烯进行二羟基化，导致末端烯烃而非内部取代度更高的烯烃发生高度区域选择性的二羟基化。这些发现现在允许在存在预先存在的内烯烃的基材上使用烯丙基金属试剂。所得二醇可以裂解为醛，以便进行后续转化。该选择性是通过与内烯烃相邻的烯丙基甲硅烷基醚所施加的空间效应来控制的。 (C) 1997 爱思唯尔科学有限公司。
Non-conjugated dienes were dihydroxylated using the commercially available osmium tetroxide AD-mix-alpha reagent resulting in highly regioselective dihydroxylation of the terminal olefin rather than the internal, more substituted olefin. These findings now allow for the use of allylmetal reagents on substrates where preexisting internal olefins are present. The resultant diol can be cleaved to the aldehyde allowing for subsequent transformations. This selectivity is controled by a steric effect imposed by the allylic silyl ether adjacent to the internal olefin. (C) 1997 Elsevier Science Ltd.