Tandem metathesis reactions cascade ring-openinig metathesis (ROM)-ring-closing metathesis (RCM)-cross metathesis dimerization (CMD) in 7-oxabiciclo[2.2.1]-hept-5-ene (7-oxanorbornene) derivatives

Heterocycles

Volumn 77, Issue 2, 2009, Pages 1333-1340

  Aljarilla, Ana ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

2,6 Dioxabicyclo 4,3,0 nonane Skeleton; Cross Metathesis Dimerization; Metathesis Reaction; Oxabicyclic Compound; Tandem Reaction

Indexed keywords

EID: 72949098475     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)45     Document Type: Article

References (52)

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39. 2, N) could induce the formation of the related tricyclic systems. See, for instance, references 8i and 8m. This possibility has been omitted in Scheme 1 for simplicity.
40. Only the specific case showed in Scheme 2 had, to the best of our knowledge, been reported for this tandem reaction. See O. Arjona, A.G. Csk, M.C. Murcia, J. Plumet, and M.B. Mula J. Organometal. Chem. 627 2001 105
41. For selected cases see reference 4. Other specific applications may be found in: J. A. Love, in Olefin Methahesis Strategies in the Synthesis of Biologically Relevant Molecules. Ref. 1a, Vol. 2, Chp. 9, pp. 296-352
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47. CMD reactions have been employed in the synthesis of macrocyclic compouds such as cylindrophanes A and F (see: A.B. Smith III, S.A. Kozmin, C.M. Adams, and D.V. Paone J. Am. Chem. Soc. 122 2000 4984
48. and references therein), [3]-catenane (see H. Iwamoto, K. Itoh, H. Nagamiya, and Y. Fukazawa Tetrahedron Lett. 44 2003 5773
49. ) and paracyclophanes (see C.J. Tae, and Y.K. Yang Org. Lett. 5 2003 741
50. ). For a review on CM reactions including synthetic applications see: S.J. Connon, and S. Blechert Angew. Chem. Int. Ed. 42 2003 1900
51. Analogous dimeric material was detected (LC-MS analysis) in a related process. See reference 81 p. 2743.
52. For recent review, see: J.D. More Org. Prep. Proc. Int. 39 2007 107