Synthesis of α,α-Difluorinated Phosphonate pSer/pThr Mimetics via Rhodium-Catalyzed Asymmetric Hydrogenation of β-Difluorophosphonomethyl α-(Acylamino)acrylates,Organic Letters

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Synthesis of α,α-Difluorinated Phosphonate pSer/pThr Mimetics via Rhodium-Catalyzed Asymmetric Hydrogenation of β-Difluorophosphonomethyl α-(Acylamino)acrylates
Organic Letters ( IF 4.9 ) Pub Date : 2018-05-21 00:00:00 , DOI: 10.1021/acs.orglett.8b01151
Hong-Xue Chen ₁ , Jie Kang ₁ , Rong Chang ₁ , Yun-Lai Zhang ₁ , Hua-Zhen Duan ₁ , Yan-Mei Li ₁ , Yong-Xiang Chen ₁

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A novel and facile synthetic strategy for α,α-difluorinated phosphonate mimetics of phosphoserine/phosphothreonine utilizing rhodium-catalyzed asymmetric hydrogenation was developed. The dehydrogenated substrate β-difluorophosphonomethyl α-(acylamino)acrylates were first prepared from protected serine/threonine followed by asymmetric hydrogenation using the rhodium–DuPhos catalytic system to generate the chiral center(s). These important phosphonate building blocks were successfully incorporated into phosphatase-resistant peptides, which displayed similar inhibition to the 14-3-3 ζ protein as the parent pSer/pThr peptides.

中文翻译：

β-二氟膦酰基甲基α-（酰基氨基）丙烯酸酯的铑催化不对称加氢合成α，α-二氟膦酸酯pSer / pThr模拟物

提出了利用铑催化的不对称加氢合成磷酸丝氨酸/磷酸苏氨酸的α，α-二氟代膦酸酯模拟物的简便方法。脱氢的底物β-二氟膦酰基甲基α-（酰基氨基）丙烯酸酯首先由受保护的丝氨酸/苏氨酸制备，然后使用铑-DuPhos催化系统进行不对称氢化以生成手性中心。这些重要的膦酸酯结构单元已成功地掺入抗磷酸酶的肽中，与亲本pSer / pThr肽相比，其显示出与14-3-3ζ蛋白相似的抑制作用。

更新日期：2018-05-21

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