Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9‐BBN provided a thermodynamically stable (E)‐allylic alcohol after oxidative work‐up, the reaction of an identical allene with HB(Sia)₂ (disiamylborane) formed a (Z)‐allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.

中文翻译：

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异戊二烯的立体发散氢硼化

报告了烯丙基的立体发散氢硼化的全部细节。用9-BBN对烯丙基进行硼氢化处理可在氧化后提供热力学稳定的（E）-烯丙基醇，而相同的烯丙基与HB（Sia）₂（二亚氨基硼烷）的反应则形成了（Z）-烯丙基醇。动力学产物。发达的条件允许以高度立体选择性的方式合成三取代的烯烃，这被认为是具有挑战性的。该方法还用于结构基序的立体发散合成，例如跳过的二烯和烯丙基苯通常嵌入生物活性天然产物中。