Department of Chemistry, Merkert Chemistry Center , Boston College , Chestnut Hill , Massachusetts 02467 , United States.
Org Lett. 2019 Feb 15;21(4):984-988. doi: 10.1021/acs.orglett.8b03959. Epub 2019 Jan 29.
An efficient method for the coupling of N-alkylamines with silicon enolates to generate β-amino carbonyl compounds is disclosed. These reactions proceed by activation of α-amino C-H bonds by B(CF), which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetine.
本文公开了一种高效的方法，用于将 N- 烷基胺与硅烯醇盐偶联，生成β-氨基羰基化合物。这些反应通过 B(CF) 激活α-氨基 C-H 键来进行，这可能会在存在大体积的 N- 烷基胺时生成一种“受阻”的酸碱配合物。该转化不需要外部氧化剂，并释放出硅烷作为副产物。该方法在西酞普兰、阿托西汀和氟西汀等生物活性分子的后期官能化中得到了验证。
