Some allylic substituent effects in ring-closing metathesis reactions: Allylic alcohol activation

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1123-1125

  Hoye, Thomas R ^a   Zhao, Hongyu ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; PROPANOL;

ARTICLE; CHEMISTRY; KINETICS;

KINETICS; PROPANOLS;

EID: 0033533652     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990947+     Document Type: Article

References (12)

1. (a) Grubbs R. H.; Chang S Tetrahedron 1998, 54, 4413-4450.
2. (b) Schuster M.; Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2056.
3. Ulman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489.
4. For a study of the effect of various substituents (including hydroxymethyl) on the ring-opening polymerization by 1 of a series of 3-substituted cyclobutenes, see: Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459-3469.
5. Three RCM reactions involving tertiary allylic alcohols were reported recently: (a) Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300.
6. (b) Sellier, O.; Van de Weghe, P.; Eustache, J. Tetrahedron Lett. 1999, 40, 5859-5860.
7. (c) Wood, J. L.; Holubec, A. A.; Stoltz, B. M.; Weiss, M. M.; Dixon, J. A.; Doan, B. D.; Shamji, M. F.; Chen, J. M.; Heffron, T. P. J. Am. Chem. Soc. 1999, 121, 6326-6327.
8. E.g., citronellene (2c) has been previously ring-closed with the Dupont tungsten metathesis catalyst. Nugent, W. A.; Feldman, J.; Calabrese, J. J. Am. Chem. Soc. 1995, 117, 8992-8998.
9. 13C NMR, IR, and HRMS data.
10. A representative plot of change in product ratios with time (and % conversion) is shown here for the 2b/2c competition experiment. Competition between citronellene (2c) and linalool (2b) in RCM reaction (4 mol% LnRu=CHPh) (figure presented)
11. Hoye, T. R.; Zhao, H. Org. Lett. 1999, 1, 169-171.
12. Crimmins, M. T.; King, B. W.; J. Org. Chem. 1996, 61, 4192-4193.