Selective domino ring-closing metathesis - Cross-metathesis reactions between enynes and electron-deficient alkenes

Organic Letters

Volumn 5, Issue 11, 2003, Pages 2007-2009

  Royer, Frédérique ^a   Vilain, Claire ^a   Elkaïm, Laurent ^a   Grimaud, Laurence ^a  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALKENE; ALKYNE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS METATHESIS; ELECTRON; RING CLOSING METATHESIS;

EID: 0141563501     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034620r     Document Type: Article

References (20)

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6. For recent reviews, see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2067. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Blechert, S. Pure Appl. Chem. 1999, 71, 1393. (f) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
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18. A previous example of a CM between a diene and an alkene was reported by Blechert et al. (in ref 7, see footnote 7).
19. More substituted vinyl alkylidene is the more stable one according to: Ulman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484.
20. If this is the case, the process is a pseudo-domino one as described in: Poli, G.; Giambastiani, G. J. Org. Chem. 2002, 67, 9456-9459.