P-Stereogenic Phosphonates via Dynamic Kinetic Resolution: A Route towards Enantiopure Tertiary Phosphine Oxides - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2019

P-Stereogenic Phosphonates via Dynamic Kinetic Resolution: A Route towards Enantiopure Tertiary Phosphine Oxides

Résumé

Asymmetric synthesis of P-stereogenic phosphonates presents a great challenge. Following this target we disclose herein a DKR strategy towards the O-P coupling reaction between an easily accessible enantiopure phenol bearing a chiral sulfinyl auxiliary and a commercially available or easily accessible racemic H-phosphinate. Although moderate to high chiral P-stereogenic organophosphorus compounds are an important class of valuable products with widespread applications particularly in asymmetric catalysis. [1] Over the last twenty years the synthesis of molecules with a P-stereogenic center has received significant attention. [2] Accordingly, several modern approaches such as enantioselective metal-couplings and C-H activation based reactions have been reported. [3] Besides, the development of chiral separation techniques provided an alternative approach. [4] However, these transformations are generally strongly limited by the generation of only specific P-stereogenic scaffolds and/or are inadequate for a large-scale synthesis. Accordingly, diastereoselective synthesis of P-stereogenic compounds, calling for a use of an enantiopure auxiliary, is still the most general and widely applied methodology to build up an array of P-stereogenic molecules. Indeed, already in 1967 Mislow had illustrated a great potential of cheap and abundant menthol for the resolution of tertiary phosphines. [5] Due to the versatility of this diastereoselective approach, this method greatly contributed to the design of P-stereogenic ligands such as DiPAMP or Mini-Phos, and their applications in asymmetric catalysis (Scheme 1a). [6] Later Jugé showed that chiral amines such as ephedrine were also very powerful chiral auxiliaries delivering the corresponding P-stereogenic oxazaphospholidine in high yield and diastereoselectivity (Scheme 1b). [7] Similar strategies developed by Han in 2013 and Framery in 2015 involved [a]
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hal-02410836 , version 1 (15-12-2020)

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Aabid Mohd, Thippani Anitha, Kallu Rajender Reddy, Joanna Wencel-Delord, Françoise Colobert. P-Stereogenic Phosphonates via Dynamic Kinetic Resolution: A Route towards Enantiopure Tertiary Phosphine Oxides. European Journal of Organic Chemistry, 2019, ⟨10.1002/ejoc.201901475⟩. ⟨hal-02410836⟩
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