Pelz Nicholas F, Morken James P
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Org Lett. 2006 Sep 28;8(20):4557-9. doi: 10.1021/ol0616891.
Chiral allyl vinyl boronates are generated by catalytic enantioselective diboration of prochiral allenes. They may then be reacted, in situ, with a hydroborating reagent to form a novel triboron intermediate. The least hindered and most reactive C-B bond then participates in cross-coupling wherein the coupling is brought about by the same catalyst as that which catalyzed the diboration reaction. The remaining C-B bonds are then oxidized in the reaction workup, thereby allowing for the modular synthesis of chiral diols in a concise single-pot fashion.
手性烯丙基乙烯基硼酸酯是通过前手性丙二烯的催化对映选择性双硼化反应生成的。然后，它们可以原位与硼氢化试剂反应，形成一种新型的三硼中间体。位阻最小且反应活性最高的C-B键随后参与交叉偶联反应，其中偶联反应由催化双硼化反应的相同催化剂引发。在反应后处理过程中，其余的C-B键被氧化，从而能够以简洁的单步方式进行手性二醇的模块化合成。
