Diastereoselective ring closing metathesis reactions: Synthesis of bicyclic diallylic alcohols and ethers

Angewandte Chemie - International Edition

Volumn 38, Issue 1-2, 1999, Pages 129-131

  Lautens, Mark ^a   Hughes, Gregory ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Bicycles; Homogeneous catalysis; Metathesis; Rearrangements

Indexed keywords

HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; MEVINOLIN;

ARTICLE; CATALYSIS; ORGANIC CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0033556066     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990115)38:1/2<129::aid-anie129>3.0.co;2-i     Document Type: Article

References (21)

1. For several recent reviews, see a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
2. b) M. S. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056;
3. b) M. S. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056;
4. c) A. Fürstner, Top. Catal. 1997, 4, 285-299;
5. d) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388;
6. e) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452;
7. f) R. H. Grubbs, S. H. Pine in Comprehensive Organic Synthesis. Vol. 5 (Ed.: B. M. Trost). Permagon, New York, 1991, pp. 1115-1127.
8. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110.
9. R. R. Schrock, J. S. Murdzek, G. C. Bazan, J, Robbins, M. DiMare, M. O'Regan, J. Am. Chem. Soc. 1990, 112, 3875-3886.
10. C.M. Huwe, J. Velder, S. Blechert. Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378.
11. C.M. Huwe, J. Velder, S. Blechert. Angew. Chem. 1996, 108, 2542-2544; Angew. Chem. Int. Ed. Engl. 1996, 35, 2376-2378.
12. a) B. Schmidt, T. Sattelkau, Tetrahedron 1997, 53, 12991-13000;
13. b) S. J. Miller, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 5855-5856;
14. c) S. J. Miller, S.-H. Kim, Z.-R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108-2109.
15. A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
16. Tetraenes 3-5 and trienes 12-15 were prepared effeciently from dimethyl malonate by dialkylation and Krapcho decarboxylation followed by addition of two equivalents of vinylcerium and protection of the resulting tertiary diallylic alcohol. See supporting information for a detailed description of the starting material preparations.
17. 1H NMR spectroscopy. See supporting information for the reactions carried out to prove the stereochemistry.
18. J. P. A. Harrity, M. S. Visser, J. D. Gleason, A. H. Hoveyda, J. Am. Chem. Soc. 1997, 119, 1488-1489.
19. a) H. Priepke, R. Brückner, Chem. Ber. 1990, 123, 153-168;
20. b) W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481-1487;
21. c) W. C. Still, A. Mitra, J. Am. Chem. Soc. 1978, 100, 1927-1928.