Synlett 2016; 27(03): 455-460
DOI: 10.1055/s-0035-1560806
letter
© Georg Thieme Verlag Stuttgart · New York

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

Jang Won Park
a   Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea   Email: ykchung@snu.ac.kr
,
Ji Eun Park
a   Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea   Email: ykchung@snu.ac.kr
,
Ji Hoon Park
a   Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea   Email: ykchung@snu.ac.kr
,
Mi Ra Hong
a   Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea   Email: ykchung@snu.ac.kr
,
Soo Min Kim
a   Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea   Email: ykchung@snu.ac.kr
,
Young Keun Chung*
a   Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Republic of Korea   Email: ykchung@snu.ac.kr
,
Chong Hyeak Kim
b   Center for Chemical Analysis, Korea Research Institute of Chemical Technology, Daejeon 305-600, Republic of Korea
› Author Affiliations
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

 
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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.