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Synlett 2021; 32(19): 1957-1962
DOI: 10.1055/a-1623-1490
DOI: 10.1055/a-1623-1490
letter
A Rh(II)- or Ag(I)-Catalyzed Formal C–O Bond Insertion of Cyclic Hemiaminal with Aryl Diazoacetate
Support for this research from the National Natural Science Foundation of China (21971262, 92056201), Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery (2019B030301005), and The Program for Guangdong Introducing Innovative and Entrepreneurial Teams (No. 2016ZT06Y337) is greatly acknowledged.
Abstract
A mild and facile synthetic method via convergent assembly of two reactive intermediates generated in situ has been developed. This method provides an efficient way to construct six- and seven-membered N-heterocycles containing a biaryl linkage. This reaction features a gem-difunctionalization process of diazo compounds with cyclic hemiaminals, delivering α-hydroxyl-β-amino ester derivatives with a tertiary carbon center through a formal C–O bond-insertion transformation.
Key words
metal carbene - cyclic hemiaminals - α-hydroxyl-β-amino esters - N-heterocycles - atom economySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1623-1490.
- Supporting Information
- CIF File
Publication History
Received: 10 August 2021
Accepted after revision: 30 August 2021
Accepted Manuscript online:
30 August 2021
Article published online:
14 September 2021
© 2021. Thieme. All rights reserved
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- 21 General Procedure for the Ag(I)-Catalyzed Formal C–O Insertion Reaction To a solution of AgOTf (25.6 mg, 10 mol%) and hemiaminal 1 (1.0 mmol) in dichloromethane (7.5 mL) was added a solution of aryldiazoacetate 2 (1.5 mmol) in dichloromethane (5.0 mL) over 15 min via a syringe pump at room temperature under argon atmosphere. The reaction was continued for an additional 2 h under these conditions. Upon completion of the reaction (monitored by TLC), the solvent was removed, and the crude product was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate = 30:1 to 10:1) to give 3 in high to excellent yields as a colorless oil. 3a-1: Yield: 120 mg (52%); colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.42–7.34 (m, 3 H), 7.25–7.18 (m, 6 H), 7.10–7.06 (m, 1 H), 7.02–6.99 (m, 3 H), 6.10 (s, 1 H), 4.95 (d, J = 13.6 Hz, 1 H), 3.85 (d,J = 13.6 Hz, 1 H), 3.75 (s, 3 H), 3.25 (brs, 1 H), 1.53 (s, 9 H). 13C NMR (100 MHz, CDCl3): δ = 174.9, 155.6, 142.5, 140.3, 138.7, 135.1, 134.0, 133.4, 129.4, 129.3, 128.8, 128.7, 128.5, 127.8, 127.2, 127.1, 127.0, 127.0, 81.1, 80.6, 69.3, 53.4, 49.2, 28.6. HRMS (ESI): m/z [M + H]+ calcd for C28H30NO5 +: 460.2118; found: 460.2121. 3a-2: Yield: 94 mg (40%); colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.56 (d,J= 7.5 Hz, 1 H), 7.52 (d, J = 8.0 Hz, 3 H), 7.47–7.43 (m, 2 H), 7.37–7.34 (m, 3 H), 7.26–7.20 (m, 4 H), 6.16 (s, 1 H), 4.85 (s, 1 H), 3.87 (d,J= 14.0 Hz, 1 H), 3.50 (s, 3 H), 1.19 (s, 9 H). 13C NMR (100 MHz, CDCl3): δ = 173.5, 155.3, 141.9, 140.2, 138.8, 135.5, 135.2, 132.2, 129.8, 129.7, 128.8, 128.5, 128.4, 128.2, 127.8, 127.5, 127.5, 126.6, 82.4, 80.5, 68.3, 52.9, 49.3, 28.1. HRMS (ESI): m/z [M + H]+ calcd for C28H30NO5 +: 460.2118; found: 460.2126. General Procedure for Rh(II)-Catalyzed Formal C–O Insertion Reaction To a solution of Rh2(OAc)4 (8.8 mg, 2 mol%) and hemiaminal 4 (1.0 mmol) in 1,2-dichloroethane (7.5 mL) was added a solution of aryldiazoacetate 2 (1.5 mmol) in dichloromethane (5.0 mL) over 20 min via a syringe pump at room temperature under argon atmosphere. The reaction was continued for an additional 2 h under these conditions. After the reaction completed (monitored by TLC), the solvent was removed, and the crude product was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate = 25:1 to 5:1) to give 5 in high to excellent yields as colorless oil. 5a-1: Yield: 195 mg (43%); colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.77–7.71 (m, 4 H), 7.42 (s, 1 H), 7.32–7.18 (m, 6 H), 6.91 (t, J = 7.4 Hz, 1 H), 6.39 (d, J = 7.6 Hz, 1 H), 6.34 (s, 1 H), 3.84 (s, 3 H), 3.19 (s, 1 H), 1.47 (s, 9 H); 13C NMR (100 MHz, CDCl3): δ = 174.1, 153.0, 137.9, 135.8, 132.8, 131.9, 129.5, 128.2, 128.1, 128.0, 127.3, 127.2, 126.7, 126.6, 125.0, 123.3, 123.0, 83.2, 81.7, 61.8, 53.5, 28.2. HRMS (ESI): m/z [M + Na]+ calcd for C27H27NNaO5 +: 468.1781; found: 468.1781. 5a-2: Yield: 201 mg (46%); white solid. 1H NMR (400 MHz, CDCl3): δ = 7.84 (d, J = 8.0 Hz, 1 H), 7.75 (d,J = 7.6 Hz, 1 H), 7.68 (d,J = 6.8 Hz, 2 H), 7.40 (t,J = 7.4 Hz, 1 H), 7.34–7.19 (m, 7 H), 6.96 (s, 1 H), 6.58 (s, 1 H), 3.81 (s, 3 H), 3.03 (s, 1 H), 1.26 (s, 9 H); 13C NMR (100 MHz, CDCl3): δ = 173.4, 152.7, 138.1, 136.1, 133.5, 132.7, 129.2, 128.6, 128.0, 127.6, 127.5, 127.0, 126.6, 126.5, 124.5, 123.4, 122.9, 83.8, 81.4, 77.3, 53.4, 28.0. HRMS (ESI): m/z [M + Na]+ calcd for C27H27NNaO5 +: 468.1781; found: 468.1781.
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