Platinum-catalyzed tandem diboration/intramolecular allylboration: Diastereoselective access to cyclohexanes bearing 1,3-diols
Platinum-catalyzed tandem diboration/intramolecular allylboration: Diastereoselective access to cyclohexanes bearing 1,3-diols
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DOI：
10.1055/s-2004-822379
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发表时间：
2004-06-18
影响因子：
2.6
通讯作者：
Morken, JP
中科院分区：
文献类型：
--
作者：
Ballard, CE;Morken, JP
由铂催化的1，3-二烯的二硼化反应，然后分子内烯丙基硼化和氧化水解组成的串联反应序列已被开发用于构建带有1，3-二醇的环状结构。该方法已被证明可有效地从二烯醛以良好的产率（44-64%）合成环己烷，以产生含有两个新的邻位立构中心的二醇，其中一个是季中心。产物以高的区域和非对映异构体比率（>19：1）获得。底物上预先存在的立构中心可以在产物中提供高水平的不对称诱导。
A tandem reaction sequence consisting of platinum-catalyzed diboration of 1,3-dienes followed by intramolecular allylboration and oxidative hydrolysis has been developed for constructing cyclic structures that bear a 1,3-diol. This methodology has proven effective for synthesizing cyclohexanes from dienals in good yields (44-64%) to generate diols containing two new vicinal stereocenters, one of which is quaternary. The products are obtained in high regio- and diastereomeric ratios (>19:1). A preexisting stereocenter on the substrate can provide high levels of asymmetric induction in the product.