High-Throughput Ligand Screening Enables the Enantioselective Conjugate Borylation of Cyclobutenones to Access Synthetically Versatile Tertiary Cyclobutylboronates was written by Clement, Helen A.;Boghi, Michele;McDonald, Rory M.;Bernier, Louise;Coe, Jotham W.;Farrell, William;Helal, Christopher J.;Reese, Matthew R.;Sach, Neal W.;Lee, Jack C.;Hall, Dennis G.. And the article was included in Angewandte Chemie, International Edition in 2019.Recommanded Product: 77876-39-2 This article mentions the following:
Cyclobutane rings are important in medicinal chem., yet few enantioselective methods exist to access this scaffold. In particular, cyclobutylboronates are receiving increasing attention in the literature due to the synthetic versatility of alkylboronic esters and the increasing role of boronic acids in drug discovery. Herein, a conjugate borylation of α-alkyl,β-aryl/alkyl cyclobutenones is reported leading to the first synthesis of enantioenriched tertiary cyclobutylboronates. Cyclobutanones with two stereogenic centers are obtained in good to high yield, with high enantioselectivity and diastereoselectivity. Vital to this advance are the development of a novel approach to α,β unsym. disubstituted cyclobutenone substrates and the use of a high-throughput chiral ligand screening platform. The synthetic utility of both the boronic ester and ketone functionalities is displayed, with remarkable chemoselectivity for either group being possible in this small ring scaffold. In the experiment, the researchers used many compounds, for example, (2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) (cas: 77876-39-2Recommanded Product: 77876-39-2).
(2S,4S)-Pentane-2,4-diylbis(diphenylphosphine) (cas: 77876-39-2) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.Recommanded Product: 77876-39-2
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis