Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
J Am Chem Soc. 2010 Jun 16;132(23):7881-3. doi: 10.1021/ja103041u.
A highly enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols 4 via aldehyde allylboration reactions of the double-chiral allylborane reagent 2a is reported. Allylborane 2a was generated from the hydroboration of commercially available allenylstannane 1 with ((d)Ipc)(2)BH at -40 to -20 degrees C followed by a kinetically controlled and highly diastereoselective 1,3-boratropic shift in intermediate 3a.
本文报道了通过双手性烯丙基硼烷试剂 2a 的醛烯丙基硼化反应,高对映选择性合成(E)-δ-锡代同型烯丙醇 4。烯丙基硼烷 2a 是由商业可得的烯丙基锡烷 1 与((d)Ipc)(2)BH 在-40 至-20°C 下进行硼氢化反应生成的,随后在中间体 3a 中发生动力学控制和高度非对映选择性的 1,3-硼迁移重排。