Re-evaluation of P-Chiral, N-Phosphoryl Sulfonamide Brønsted Acids in the Asymmetric Synthesis of 1,2,3,4-Tetrahydroquinoline-2-carboxylate Esters via Biomimetic Transfer Hydrogenation

Abstract

Enantioenriched heterocyclic and rigidified bioisosteres of amino acids are valuable building blocks in drug discovery, particularly in the design of peptidomimetic drugs. The rigidified bioisostere of phenylalanine, 1,2,3,4-tetrahydroquinoline-2-carboxylic acid, is found in several biologically active compounds. However, only a small number of successful methodologies have been reported for its asymmetric synthesis. To develop an environmentally benign and metal-free organocatalytic process for the preparation of this compound, a number of novel P-chiral, N-phosphoryl sulfonamide Brønsted acids were synthesized and evaluated in a biomimetic transfer hydrogenation reaction of quinoline-2-carboxylates to give the (R)-1,2,3,4-tetrahydroquinoline-2-carboxylates.

Key words

Brønsted acid catalysis - transfer hydrogenation - asymmetric synthesis

Publication History

Received: 28 December 2022

Accepted after revision: 06 March 2023

Accepted Manuscript online:
06 March 2023

Article published online:
06 April 2023

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• 44 An oven-dried pressure vessel was cooled to ambient temperature in a desiccator and charged with methyl quinoline-2-carboxylate (188 mg, 1.00 mmol), Hantzsch ester (634 mg, 2.50 mmol) and 14e (25.2 mg, 0.0501 mmol). Subsequently, anhydrous cyclohexane (5.0 mL) was added. The vial was capped, and the mixture was stirred vigorously at 50 °C for 4 h. The resulting solution was diluted with DCM (2.5 mL) and SiO₂ was added. The mixture was concentrated in vacuo and the crude material was first purified on Et₃N-deactvated SiO₂ by flash chromatography (0–3% EtOAc/hexanes), with the co-elution of some Hantzsch pyridine by-product. Purification by flash column chromatography on SiO₂ (0–5% EtOAc/hexanes) afforded the desired product 8 (R² = CO₂Me, R⁶=H), as a yellow oil in 69% yield (130 mg, 0.681 mmol) and 46% ee. Chiral HPLC method: Chiralpak AD, hexane/IPA = 80:20, 1 mL/min, λ = 254 nm; t_R = 6.49 [(R)-, major], 7.78 [(S)-, minor] min. ¹H NMR (400 MHz, CDCl₃): δ = 7.00 (t, J = 7.6 Hz, 1 H), 6.96 (d, J = 7.4 Hz, 1 H), 6.65 (td, J = 7.3, 1.2 Hz, 1 H), 6.59 (d, J = 8.0 Hz, 1 H), 4.36 (s, 1 H), 4.05 (dd, J = 8.8, 3.8 Hz, 1 H), 3.78 (s, 3 H), 2.84 (ddd, J = 15.1, 9.3, 5.4 Hz, 1 H), 2.75 (dt, J = 16.3, 5.5 Hz, 1 H), 2.29 (dtd, J = 13.0, 5.6, 3.8 Hz, 1 H), 2.01 (dtd, J = 12.9, 9.1, 5.2 Hz, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 173.8, 143.1, 129.3, 127.2, 120.7, 117.8, 114.7, 54.1, 52.5, 26.0, 24.8.