Rhodium-Catalyzed Intramolecular [4+4] Cycloaddition of Bisdienes To Form Ring-Condensed 1,5-Cyclooctadienes

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.

Key words

cycloaddition - rhodium - catalysis - polycycles

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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: [phone]; E-mail: [e-mail]; 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.