Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters

Diao Chen; Jian-Guo Liu; Xu Zhang; Ming-Hua Xu

doi:10.1055/s-0037-1610722

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(14): 1693-1697
DOI: 10.1055/s-0037-1610722

cluster

Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Glyoxylates: Access to Optically Active Substituted Mandelic Acid Esters

Diao Chen

^aState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China

,

Jian-Guo Liu

^bShenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen 518055, P. R. of China eMail: xumh@sustech.edu.cn

,

Xu Zhang

^aState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China

,

Ming-Hua Xu ∗

^aState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China

^bShenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Shenzhen 518055, P. R. of China eMail: xumh@sustech.edu.cn

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Abstract

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^◊ D.C. and J.G.L. contributed equally.Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis

Abstract

A rhodium-catalyzed enantioselective addition of glyoxylates to arylboronic acids promoted by a simple chiral sulfinamide-based olefin ligand under mild reaction conditions is described. The reaction provides access to a variety of optically active substituted mandelic acid esters in good yields with up to 83% ee. The catalytic system is also applicable to pyruvate addition. The synthetic utility of this method is highlighted by a formal synthesis of the antiplatelet drug clopidogrel.

Key words

asymmetric catalysis - rhodium catalysis - ligands - mandelic acid esters - glyoxylate - arylboronic acids

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Referenzen

References and Notes

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17 Isopropyl Aryl(hydroxy)acetates 3a–q; General ProcedureUnder an Ar atmosphere, a solution of the appropriate glyoxylate 1 (0.2 mmol), [Rh(COE)₂Cl]₂ (1.5 mol%), L12 (3.3 mol%), and arylboronic acid (0.4 mmol) in 1,4-dioxane (2 mL) was stirred at r.t. for 30 min. 0.1 M aq KOH (0.1 mL, 0.01 mmol) was then added and the resulting mixture was stirred 40 °C for 5 h until the starting materials disappeared (TLC). The solvent was evaporated under vacuum and the residue was purified by column chromatography (silica gel).
18 Isopropyl (2S)-(3,4-Dimethoxyphenyl)(hydroxy)acetate (3o)White solid; yield: 38.1 mg (75%, 72% ee). ¹H NMR (400 MHz, CDCl₃): δ = 7.01–6.90 (m, 2 H), 6.84 (d, J = 8.2 Hz, 1 H), 5.07 (m, 2 H), 3.88 (d, J = 1.2 Hz, 6 H), 3.54 (s, 1 H), 1.28 (d, J = 6.2 Hz, 3 H), 1.13 (d, J = 6.3 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 173.4, 149.1, 149.0, 131.2, 119.1, 111.0, 109.4, 72.7, 70.1, 55.9, 55.9, 21.8, 21.5.Isopropyl (2S)-(3,5-Dimethoxyphenyl)(hydroxy)acetate (3q)White solid; yield: 50.3 mg (99%, 75% ee). ¹H NMR (400 MHz, CDCl₃): δ = 7.01–6.90 (m, 2 H), 6.84 (d, J = 8.2 Hz, 1 H), 5.07 (m, 2 H), 3.88 (s, 6 H), 3.54 (s, 1 H), 1.28 (d, J = 6.2 Hz, 3 H), 1.13 (d, J = 6.3 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 173.1, 160.9, 140.9, 104.4, 100.6, 73.0, 70.3, 55.4, 21.8, 21.5.

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