Trapping of Carboxylic Oxonium Ylides with N-Boc Imines for the Facile Synthesis of β-Amino Alcohol Derivatives

Abstract

A Rh₂(OAc)₄-catalyzed three-component reaction of carboxylic acids, α-diazoacetophenones, and N-Boc imines has been developed to efficiently produce β-amino alcohol derivatives. Oxonium ylides generated from carboxylic acids and metal carbenoids have been intercepted by electrophiles for the first time.

Key words

multicomponent reactions - diazo compounds - metal carbenoids - ylides - imines

• References and Notes

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• 13 1-(tert-Butoxycarbonylamino)-3-oxo-3-phenyl-1-p-tolylpropan-2-yl benzoate (4a) anti- 4a: ¹H NMR (CDCl₃, 400 MHz): δ = 8.06–7.99 (m, 4 H), 7.62–7.56 (m, 2 H), 7.49–7.42 (m, 4 H), 7.30 (d, J = 8.0 Hz, 2 H), 7.14 (d, J = 8.0 Hz, 2 H), 6.36 (d, J = 3.0 Hz, 1 H), 5.46 (s, 2 H), 2.29 (s, 3 H), 1.35 (s, 9 H); ¹³C NMR (CDCl₃, 100 MHz): δ = 194.0, 165.7, 154.9, 137.7, 135.6, 134.9, 133.8, 133.5, 129.9, 129.5, 129.1, 128.9, 128.5, 128.4, 126.5, 80.0, 77.7, 54.5, 28.2, 21.1; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₈H₂₉NNaO₅: 482.1938; found: 482.1940. syn-4a: ¹H NMR (CDCl₃, 400 MHz): δ = 8.07 (d, J = 7.5 Hz, 2 H), 7.97–7.94 (m, 2 H), 7.60–7.53 (m, 2 H), 7.47–7.41 (m, 4 H), 7.13 (d, J = 8.0 Hz, 2 H), 7.07 (d, J = 8.0 Hz, 2 H), 6.57 (s, 1 H), 5.60 (d, J = 8.1 Hz, 1 H), 5.49 (s, 1 H), 2.27 (s, 3 H), 1.42 (s, 9 H); ¹³C NMR (CDCl₃, 100 MHz): δ = 194.4, 165.8, 137.9, 135.3, 133.6, 133.4, 129.9, 129.2, 128.8, 128.7, 128.6, 128.5, 127.2, 80.0, 77.3, 76.5, 55.4, 28.3, 21.0; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₈H₂₉NNaO₅: 482.1938; found: 482.1944.
• 14 Three-Component Reaction of Benzoic Acid with α-Diazoacetophenone and N-Boc Imine; General Procedure: Under an argon atmosphere, to a mixture of Rh₂(OAc)₄ (0.003 mmol), benzoic acid 1 (0.36 mmol), N-Boc imine 3 (0.30 mmol), and 4 Å MS (100 mg) in toluene (4.0 mL) stirred at 40 °C, was added α-diazoacetophenone 2 (0.36 mmol) in toluene (2.0 mL) by using a syringe pump over 1 h. Upon complete addition, the solvent was removed, and a portion of crude product was subjected to ¹H NMR analysis to determine the diastereomeric ratio. The crude product was purified by column chromatography on silica gel to obtain the corresponding product 4.

Similar rate-accelerating effects for N-Boc imines bearing electron-donating substituents on the aryl rings have been observed, see:
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• 16 We have filed a patent application for this three-component reaction, see: CN102391154, 2011.