由脂肪醛通过酸度导向合成取代γ-丁内酯
Acidity-directed synthesis of substituted gamma-butyrolactones from aliphatic aldehydes.
作者信息
Ramachandran P Veeraraghavan, Pratihar Debarshi
机构信息
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
出版信息
Org Lett. 2007 May 24;9(11):2087-90. doi: 10.1021/ol0705806. Epub 2007 May 1.
The strength of the Lewis or Brønsted acids controls the formation of either beta,gamma-disubstituted-alpha-methylene-gamma-butyrolactones or gamma-substituted-alpha-alkylidene-gamma-butyrolactones via the lactonization or oxonia cope rearrangement-lactonization, respectively, of the borate intermediates resulting from the crotylboration of aliphatic aldehydes with ester-containing crotylboronates, such as (E)-methyl 2-boramethyl-2-butenoates.
路易斯酸或布朗斯特酸的强度分别通过含酯巴豆硼酸酯（如（E）-2-硼甲基-2-丁烯酸甲酯）对脂肪醛进行巴豆基硼化反应生成的硼酸酯中间体的内酯化反应或氧杂科普重排-内酯化反应，控制β,γ-二取代-α-亚甲基-γ-丁内酯或γ-取代-α-亚烷基-γ-丁内酯的形成。
Zotero 插件