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Synlett 2014; 25(6): 853-857
DOI: 10.1055/s-0033-1340715
DOI: 10.1055/s-0033-1340715
letter
N-Heterocyclic Carbene Mediated Homoenolate Annulation of Benzofuran-2,3-diones: Stereoselective Synthesis of Bis-Spirofuranones
Further Information
Publication History
Received: 19 November 2013
Accepted after revision: 13 January 2014
Publication Date:
10 February 2014 (online)
Abstract
Stereoselective synthesis of bis-spirofuranones via N-heterocyclic carbene catalyzed homoenolate annulations of benzofuran-2,3-diones is reported.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References and Notes
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- 28 Synthesis of 3′-(4-Methoxyphenyl)-4,7-dimethyl-2H,3′H-spiro[benzofuran-3,2′-furan]-2,5′(4′H)-dione (4a) 4,7-Dimethylbenzofuran-2,3-dione (88 mg, 0.5 mmol), 4-methoxycinnamaldehyde (122 mg, 0.75 mmol), and carbene precursor (15 mol%) were taken in dry CH2Cl2 (5 mL). After addition of Et3N (20 mol%) the reaction mixture was refluxed at 40 °C for 5 h under argon atmosphere. The reaction mixture on column chromatography on silica gel (100–200 mesh) using an EtOAc–hexane (10:90) mixture yielded the bis-spirofuranone 4a as a white solid. Yield 143 mg (85%); mp 111–113 °C. 1H NMR (500 MHz, CDCl3): δ = 7.12 (d, J = 8.0 Hz, 1 H), 6.95 (d, J = 8.0 Hz, 1 H), 6.79 (d, J = 9.0 Hz, 2 H), 6.72 (d, J = 8.5 Hz, 2 H), 4.27 (dd, J 1 = 14.0 Hz, J 2 = 8.0 Hz, 1 H), 3.75 (s, 3 H), 3.68 (dd, J 1 = 17.0 Hz, J 2 = 14.0 Hz, 1 H), 2.90 (dd, J 1 = 17.0 Hz, J 2 = 8.5 Hz, 1 H), 2.49 (s, 3 H), 2.10 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 173.4, 171.9, 159.8, 152.3, 133.5, 133.3, 128.7, 126.8, 122.9, 119.7, 118.9, 114.2, 86.9, 55.1, 47.5, 31.2, 17.1, 14.4. IR (film): νmax = 1810, 1736 cm–1. ESI-HRMS: m/z calcd for C20H18O5 [M + Na]+: 361.10519; found: 361.10471.
For reviews on NHC catalysis, see:
For selected references for asymmetric benzoin condensation reaction, see:
For reviews on homoenolate anions and their equivalents, see:
For reviews on NHC catalyzed homoenolate chemistry, see: