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Synlett 2016; 27(03): 455-460
DOI: 10.1055/s-0035-1560806
DOI: 10.1055/s-0035-1560806
letter
Rhodium-Catalyzed Intramolecular [4+4] Cycloaddition of Bisdienes To Form Ring-Condensed 1,5-Cyclooctadienes
Further Information
Publication History
Received: 18 July 2015
Accepted after revision: 25 September 2015
Publication Date:
09 November 2015 (online)

Abstract
A novel simple synthesis of bicyclo[6.n.0] (n = 3, 4) frameworks from various bisdienes by rhodium-catalyzed [4+4] cycloaddition has been developed. The reaction tolerates carbon or heteroatoms in the tether between the diene moieties.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560806.
- Supporting Information
-
References and Notes
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- 12 The synthetic procedures and spectroscopic data for the new compounds are summarized in the Supporting Information. Crystallographic data for compounds 1b and 8b have been deposited with the accession numbers CCDC 778348 and 778347, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/ conts/retrieving.html.
- 13 (3aR*,9aS*)-2-Tosyl-2,3,3a,6,7,9a-hexahydro-1H-cycloocta[c]pyrrole (1b); Typical Procedure A solution of AgSbF6 (5.2 mg, 10 mol%) in DCE (1.0 mL) was injected from a syringe under flowing N2 into a flame-dried 15 mL Schlenk flask capped with a screw cap. [Rh(cod)Cl]2 (3.7 mg, 5 mol%) was added, and the mixture was stirred for 15 min. Bisdiene 1a (0.15 mmol) and distilled EtOAc (0.5 mL) were then added to the flask under flowing N2, and the mixture was stirred at 120 °C for 12 h. Flash chromatography (silica gel; hexane–EtOAc, 15:1) gave a white solid; yield 37 mg (82%). 1H NMR (300 MHz, CDCl3): δ = 2.02 (dd, 2 H, J = 6.5, 12.6 Hz), 2.43 (s, 3 H), 2.46–2.53 (m, 2 H), 3.11 (d, 2 H, J = 15.4 Hz), 3.15–3.19 (m, 2 H), 3.50 (d, 2 H, J = 12.2 Hz), 5.07–5.11 (m, 2 H), 5.46 (m, 2 H), 7.33 (d, 2 H, J = 8.0 Hz), 7.74 (d, 2 H, J = 8.1 Hz). 13C NMR (75 MHz, CDCl3): δ = 21.5, 27.9, 42.4, 53.4, 127.4, 128.0, 129.6, 129.7, 134.1, 143.4. HRMS (EI+): m/z calcd for C17H21NO2S+: 303.1293; found: 303.1295.
For three-membered rings, see:
For four-membered rings, see:
For five-membered rings, see:
For six-membered rings, see ref. 1e. For seven-membered rings, see:
Pd:
Ru:
Fe:
For transition metal-mediated reactions, see:
Rh:
Co:
Ru:
Ni:
Rh:
Ni: