VINYLIC ORGANOBORANES .14. A STEREOSPECIFIC SYNTHESIS OF (E)-1-HALO-1-ALKENES FROM 1-ALKYNES
VINYLIC ORGANOBORANES .14. A STEREOSPECIFIC SYNTHESIS OF (E)-1-HALO-1-ALKENES FROM 1-ALKYNES
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DOI：
10.1021/jo00287a019
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发表时间：
1989-12-22
影响因子：
3.6
通讯作者：
BHAT, NG
中科院分区：
文献类型：
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作者：
BROWN, HC;HAMAOKA, T;BHAT, NG
研究了(E)-1-烯基硼酸及其酯和(E)-1-烯基二溴硼烷-二甲基硫醚配合物在不同条件下与碘的反应。所有这些化合物在碱的存在下与碘反应，以极好的收率和很高的立体化学纯度生成(E)-1-碘-1-烯烃。本文描述了基于(Z)-1-烯基硼酸和酯的(E)-1-溴-和1-氯-1-烯烃的立体定向合成。这些反应似乎是普遍的。上述方法提供了方便的立体定向合成(E)-1-halo-1-烯烃的方法。在每种情况下都讨论了一种合理的机制。
The reactions of (E)-1-alkenylboronic acids and their esters and (E)-1-alkenyldibromoborane-dimethyl sulfide complexes with iodine under various conditions were investigated. All of these compounds react with iodine in the presence of base, producing (E)-1-iodo-1-alkenes in excellent yields and in very high stereochemical purities. A stereospecific synthesis of (E)-1-bromo- and 1-chloro-1-alkenes is herein described, based on (Z)-1-alkenylboronic acids and esters. These reactions appear to be general. The above procedures provide convenient stereospecific syntheses of (E)-1-halo-1-alkenes. A plausible mechanism in each case has been discussed.