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Synlett 2023; 34(14): 1732-1738
DOI: 10.1055/a-2014-2813
DOI: 10.1055/a-2014-2813
letter
An Efficient Route to Access Spirooxindole–Pyrazolone-Fused Cyclopentenes by a Diastereoselective [3+2] Annulation
R.G.B. thanks DST-SERB (CRG/2019/005753), Government of India, for the generous research grant. The authors also thank IISER Pune for the financial assistance. A.S.S. and P.K.W. thank UGC New Delhi, Government of India, for providing fellowships.
Abstract
A DMAP-catalyzed, highly diastereoselective, [3+2] cycloaddition of pyrazolone-derived Morita–Baylis–Hillman carbonates to 3-methyleneoxindoles has been developed. A variety of structurally diverse and complex spiropyrazolone-fused oxindoles bearing three contiguous chiral centers have been synthesized in high yields (up to 98%) and with excellent diastereoselectivities (up to 99:1). Moreover, the synthetic potential of this protocol has been demonstrated by performing a Suzuki coupling reaction.
Key words
annulation - spiropyrazolones - diastereoselectivity - Morita–Baylis–Hillman carbonates - spirooxindolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611940.
- Supporting Information
- CIF File
Publication History
Received: 05 November 2022
Accepted after revision: 16 January 2023
Accepted Manuscript online:
16 January 2023
Article published online:
11 May 2023
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- 26 Product 3a; Typical Procedure An oven-dried round-bottomed flask was charged with the MBH carbonate 1a (35 mg, 0.094 mmol), the indolinone 2a (24 mg, 0.112 mmol), DMAP (2.28 mg, 0.019 mmol), and CHCl3 (2 mL), and the mixture was stirred at rt for 12 h. When the reaction was complete (TLC), the solvent was evaporated under reduced pressure and the crude product was directly purified by column chromatography [silica gel (100–200 mesh), PE–EtOAc (70:30)] to give a brown solid; yield: 45 mg (92%, 99:1 dr); mp 78–80 °C. Rf = 0.3 (PE–EtOAc, 70:30). 1H NMR (400 MHz, CDCl3): δ = 8.0 (d, J = 7.0 Hz, 2 H), 7.6 (m, 3 H), 7.5–7.4 (m, 2 H), 7.4–7.3 (m, 3 H), 7.2–7.1 (m, 2 H), 7.1 (d, J = 2.2 Hz, 1 H), 6.8 (d, J = 25.2 Hz, 2 H), 4.9 (d, J = 2.3 Hz, 1 H), 3.7 (s, 3 H), 3.3 (s, 3 H), 2.2 (s, 3 H). 13C {1H} NMR (100 MHz, CDCl3): δ = 190.9, 174.1, 172.5, 169.1, 156.5, 144.7, 143.3, 142.8, 137.3, 136.8, 133.6, 130.1, 129.9, 128.9, 128.8, 125.9, 125.0, 124.0, 123.4, 119.7, 108.6, 67.2, 65.0, 53.8, 53.0, 26.9, 15.9. HRMS (ESI TOF): m/z [M + H]+ calcd for C31H26N3O5: 520.1872; found: 520.1876.