Synlett 2019; 30(14): 1693-1697
DOI: 10.1055/s-0037-1610722
cluster
© Georg Thieme Verlag Stuttgart · New York

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

Diao Chen
a  State 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
b  Shenzhen 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
a  State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China
,
a  State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. of China
b  Shenzhen 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
› Author Affiliations
The National Science & Technology Major Project (2018ZX09711002-006), National Natural Science Foundation of China (81521005, 21472205, 21325209)
Further Information

Publication History

Received: 31 May 2019

Accepted after revision: 25 June 2019

Publication Date:
17 July 2019 (online)


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.

Supporting Information

 
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  • 17 Isopropyl Aryl(hydroxy)acetates 3aq; 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.