Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol

Organic Letters

Volumn 7, Issue 2, 2005, Pages 187-190

  Funk, Timothy W ^a   Efskind, Jon ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 13444259632     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047929z     Document Type: Article

References (28)

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2. For recent reviews on olefin metathesis, see: (a) Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 20377-2056. (c) Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1-16. (d) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
3. For recent reviews on olefin metathesis, see: (a) Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 20377-2056. (c) Ivin, K. J. J. Mol. Catal. A: Chem. 1998, 133, 1-16. (d) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
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23. 2 group).
24. This type of vinylalkylidene stabilization has been observed by our group as well as others: (a) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845-3847. (b) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (c) See ref 3a.
25. This type of vinylalkylidene stabilization has been observed by our group as well as others: (a) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845-3847. (b) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (c) See ref 3a.
26. This type of vinylalkylidene stabilization has been observed by our group as well as others: (a) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845-3847. (b) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (c) See ref 3a.
27. Chatterjee, A. K.; Choi, T. L.; Sanders. D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
28. An overall yield of 51% was achieved when the two steps of the reaction were performed independently.