Chiral Phosphite-Olefin Ligands：Application in Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to β-Aryl-α,β-unsaturated Sulfonates

doi:10.6023/A14060436

Abstract

Chiral sulfonyl compounds have great versatility in organic synthesis, and they are also important as biologically active substances in medicinal chemistry. Among various methods developed for their synthesis, rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated sulfonyl compounds represents one of the most practical methods due to the stability and availability of the boronic acid used as a nucleophile. Although several Rh(I) complexes of bidentate ligands have been discovered for asymmetric conjugation addition of α,β-unsaturated sulfonyl compounds, some challenging issues still remain in terms of efficiency, enantioselectivity and substrate scope. Therefore, the development of an efficient catalytic system for the synthesis of chiral sulfonyl compounds is an important goal in extending the current methodology. Here, a general and mild method for the rhodium-catalyzed enantioselective catalytic conjugate addition of arylboronic acids to β-aryl-α,β-unsaturated sulfonate is described. The success of the process relies on the use of extraordinary simple chiral phosphite-olefin ligands as bidentate ligands which offer notable synthetic and economic advantages. Optimum reaction condition was determined to run the reaction at 50 ℃ using dioxane as the solvent, in the presence of 2.5 mol% of [Rh(coe)₂Cl]₂ and 5 mol% of chiral P/olefin ligand L7. This Rh(I) catalyst containing chiral P/olefin ligand has a broad substrate scope, a wide range of arylboronic acids with varying electronic and steric demands were successfully examined with α,β-unsaturated sulfonate (1). Notably, all transformations proceed efficiently to give the desired products in good yields (84%～95%) and excellent selectivities (92%～99% ee). The electronic properties of the arylboronic acids did not appear to affect the reactivity of the reaction. Besides, α,β-unsaturated sulfonate 1 with either an electron-donating or electron-withdrawing group on any aromatic carbon readily underwent the asymmetric arylation with arylboronic acids, affording chiral sulfonates in high yields and enantioselectivities. The current reaction provides a practical approach to the synthesis of diverse highly enantioenriched gem-diaryl substituted sulfonates.

Key words: asymmetric catalysis, P/olefin ligand, α,β-unsaturated sulfonate, 1,4-addition, chiral gem-diaryl compound

Cite this article

Yu Yue-Na, Xu Ming-Hua. Chiral Phosphite-Olefin Ligands：Application in Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to β-Aryl-α,β-unsaturated Sulfonates[J]. Acta Chimica Sinica, 2014, 72(7): 815-819.

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