Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene–Imine [3 + 2] Annulation,ACS Catalysis

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Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene–Imine [3 + 2] Annulation
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-05-04 00:00:00 , DOI: 10.1021/acscatal.8b01081
Andrew J. Smaligo ₁ , Sriramurthy Vardhineedi ₁ , Ohyun Kwon ₁

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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.

中文翻译：

香芹酮衍生的P-Stereogenic膦：设计，合成和在Allene-Imine [3 + 2]环中使用

我们通过从天然产物香芹酮开始的简单合成方法，制备了以前未报道的P-stereogenic [2.2.1]双环手性膦家族。该设计原理促使不可预见的C-脱烯基化反应的发展。我们已经将这些有机催化剂应用于一系列吡咯啉的不对称合成中，这些吡咯啉以高收率和对映选择性（包括具有生物活性的小分子efsevin）获得。

更新日期：2018-05-04

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