Kinsinger Thorsten, Priester Ronja, Kazmaier Uli
Organic Chemistry, Saarland University, Campus, Building C4.2, D-66123 Saarbrücken, Germany.
Org Lett. 2023 Aug 11;25(31):5902-5906. doi: 10.1021/acs.orglett.3c02199. Epub 2023 Aug 2.
Substituted allyl derivatives with an internal double bond can be homologated under standard conditions via a 1,2-shift, whereas allylboronic esters with terminal double bonds can also be homologated via a S' reaction. This allyl isomerization is catalyzed by ZnCl and can be suppressed by omitting ZnCl during the formation of α-chloroboronic ester. However, in the second step with Grignard reagents, ZnCl was added to suppress side reactions of the product formed.
具有内双键的取代烯丙基衍生物可在标准条件下通过1,2-迁移进行同系化反应，而具有末端双键的烯丙基硼酸酯也可通过S'反应进行同系化反应。这种烯丙基异构化反应由ZnCl催化，并且在α-氯硼酸酯形成过程中通过省略ZnCl可抑制该反应。然而，在与格氏试剂反应的第二步中，加入ZnCl以抑制所形成产物的副反应。
