Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland.
Molecules. 2022 Apr 6;27(7):2357. doi: 10.3390/molecules27072357.
β-Hydroxy sulfones are important in organic synthesis. The simplest method of β-hydroxy sulfones synthesis is the hydrogenation of β-keto sulfones. Herein, we report the reducing properties of alkyl aluminum compounds RAl (R = Et, -Bu, -Bu, -Bu and -Hex); -BuAlH; EtAlCl and EtAlCl in the hydrogenation of β-keto sulfones. The compounds -BuAlH, -BuAl and EtAl are the at best reducing agents of β-keto sulfones to β-hydroxy sulfones. In reactions of β-keto sulfones with aluminum trialkyls, hydroalumination products with β-hydroxy sulfone ligands [RAlOC(CH)CHS(O)(-RCH] [where = 1,2; : R = -Bu, R = CH; : R = -Bu, R = Cl; : R = Et, R = CH; : R = Et, R = Cl] and {[EtAlOC(CH)CHS(O)(-ClCH]∙EtAl} were obtained. These complexes in the solid state have a dimeric structure, while in solutions, they appear as equilibrium monomer-dimer mixtures. The hydrolysis of both the isolated , , , and and the postreaction mixtures quantitatively leads to pure racemic β-hydroxy sulfones. Hydroalumination reaction of β-keto sulfones with alkyl aluminum compounds and subsequent hydrolysis of the complexes is a simple and very efficient method of β-hydroxy sulfones synthesis.
β-羟基砜在有机合成中很重要。β-酮砜的氢化是合成β-羟基砜最简单的方法。在此，我们报告了烷基铝化合物 RAl（R = Et，-Bu，-Bu，-Bu 和 -Hex）；-BuAlH；EtAlCl 和 EtAlCl 在β-酮砜氢化中的还原性能。-BuAlH、-BuAl 和 EtAl 是将β-酮砜还原为β-羟基砜的最佳还原剂。在β-酮砜与三烷基铝的反应中，得到了具有β-羟基砜配体 [RAlOC(CH)CHS(O)(-RCH] [其中 = 1,2；：R = -Bu，R = CH；：R = -Bu，R = Cl；：R = Et，R = CH；：R = Et，R = Cl] 和 {[EtAlOC(CH)CHS(O)(-ClCH]∙EtAl} 的氢铝化产物。这些配合物在固态下具有二聚体结构，而在溶液中则表现为平衡的单体-二聚体混合物。分离得到的,,, 和 以及后反应混合物的水解定量地得到纯外消旋的β-羟基砜。β-酮砜与烷基铝化合物的氢铝化反应以及随后的配合物水解是合成β-羟基砜的一种简单而非常有效的方法。
