Spirocycle assembly through selective tandem ring closing metathesis reactions

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3247-3250

  Bassindale, Martin J ^a   Hamley, Peter ^b   Leitner, Andreas ^a   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b Astra Charnwood ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033574461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00375-5     Document Type: Article

References (16)

1. For recent reviews on the ring closing metathesis reaction in organic synthesis see: (a) Armstrong, S.K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
2. (b) Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413.
3. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
4. Metathesis of the penta-1,4-diene unit to a cyclopropene was not considered. For related references see: (a) Huwe, C.M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376.
5. (b) Michaut, M.; Parrain, J.-L.; Santelli, M. Chem. Commun. 1998, 2567.
6. (a) For example see: Barrett, A.G.M.; Baugh, S.P.D.; Gibson, V.C.; Giles, M.R.; Marshall, E.L.; Procopiou, P.A. Chem. Commun. 1996, 2231.
7. (b) For an example of cyclohexene formation over cyclopentene cyclisation see: Kirkland, T.A.; Grubbs, R.H. J. Org. Chem. 1997, 62, 7310.
8. (c) For an example of cyclohexene formation over spirocyclic cyclopentene formation see: Dyatkin, A.B. Tetrahedron Lett. 1997, 38, 2065.
9. Mutterer, F.; Morgen, J.M.; Bieldermann, J.M.; Fleury, J.P.; Weiss, F. Bull. Chim. Soc. Fr. 1979, 4478.
10. 1H NMR in comparison to an authentic sample of 7.
11. 2: 136.0524. Found: 136.0525.
12. Perron, F.; Albizati, K.F. Chem. Rev. 1989, 59, 1617.
13. For an approach to spirocycles using single ring closing metathesis see: (a) van Hooft, P.A.V.; Leeuwenburgh, M.A.; Overkleeft, H.S.; van der Marel, G.A.; van Boeckel, C.A.A.; van Boom, J.H. Tetrahedron Lett. 1998, 39, 6061.
14. (b) Maier, M.E.; Bugl, M. Synlett 1998, 1390.
15. Grubbs and co-workers have also observed that dienes containing electron withdrawing olefinic substituents are poor substrates in the ring closing metathesis reaction, see reference 3(b). For a related example see Rutjes, F.P.J.T.; Shoemaker, H.E. Tetrahedron Lett. 1997, 38, 677. The referee pointed out that the slow reaction of 15 may also be due to the unfavourable conformational change in going from ester (s-cis) to lactone (s-trans).
16. Catalyst insertion into alkenes adjacent to a quarternary centre does not take place readily at room temperature: Schwab, P.; Grubbs, R.H.; Ziller, J.W. J Am. Chem. Soc. 1996, 118, 100.