香芹酮衍生的P-手性膦：设计、合成及其在丙二烯-亚胺[3 + 2]环化反应中的应用
Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.
作者信息
Smaligo Andrew J, Vardhineedi Sriramurthy, Kwon Ohyun
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States.
出版信息
ACS Catal. 2018 Jun 1;8(6):5188-5192. doi: 10.1021/acscatal.8b01081. Epub 2018 May 4.
Abstract
We have prepared a previously unreported family of P-stereogenic [2.2.1] bicyclic chiral phosphines through straightforward syntheses starting from the natural product carvone. This design rationale prompted the development of an unforeseen C-dealkenylation reaction. We have applied these organocatalysts in the asymmetric syntheses of a bevy of pyrrolines, obtained in high yields and enantioselectivities, including a biologically active small molecule, efsevin.
摘要
我们通过从天然产物香芹酮出发的直接合成方法，制备了一族此前未报道的P-手性[2.2.1]双环手性膦。这种设计理念促使了一种意想不到的C-脱烯基化反应的发展。我们已将这些有机催化剂应用于多种吡咯啉的不对称合成中，这些吡咯啉的产率和对映选择性都很高，其中包括一种具有生物活性的小分子——埃夫西文。
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