Olefin Metathesis: Remote Substituents Governing the Stereoselectivity of 11-Membered-Ring Formation

Organic Letters

Volumn 6, Issue 2, 2004, Pages 205-208

  Vassilikogiannakis, Georgios ^a   Margaros, Ioannis ^a   Tofi, Maria ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; MACROCYCLIC COMPOUND; SPIRO COMPOUND;

ARTICLE; CHEMICAL REACTION; RING CLOSING METATHESIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0842306918     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036156w     Document Type: Article

References (14)

1. For selected recent reviews in olefin metathesis see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
2. For selected recent reviews in olefin metathesis see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
3. For selected recent reviews in olefin metathesis see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
4. For selected recent reviews in olefin metathesis see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
5. Nicolaou, K. C.; Vassilikogiannakis, G.; Montagnon, T. Angew. Chem., Int. Ed. 2002, 41, 3276.
6. For the preparation of the catalyst see: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
7. For examples of the synthesis of 11-membered rings by using olefin metathesis see: (a) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043. (b) Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 1873. (e) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
8. For examples of the synthesis of 11-membered rings by using olefin metathesis see: (a) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043. (b) Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 1873. (e) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
9. For examples of the synthesis of 11-membered rings by using olefin metathesis see: (a) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043. (b) Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 1873. (e) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
10. For examples of the synthesis of 11-membered rings by using olefin metathesis see: (a) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043. (b) Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 1873. (e) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
11. For examples of the synthesis of 11-membered rings by using olefin metathesis see: (a) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043. (b) Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429. (d) Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 1873. (e) Fürstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehmann, C. W.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
12. Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 2826.
13. 14,15) was unambiguously confirmed by extensive nOe studies.
14. 7,8) of 7d were independently treated with Grubbs' catalyst after their careful chromatographic separation. The reaction conditions and the yields were similar for both.