Diastereoselectivity in a ring closing metathesis reaction with a remote stereogenic centre leading to quaternary dihydropyrans

Tetrahedron

Volumn 56, Issue 16, 2000, Pages 2421-2426

  Schmidt, Bernd ^a   Westhus, Markus ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Diastereoselectivity; Dihydropyrans; Metathesis reaction

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034647019     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00150-2     Document Type: Article

References (21)

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14. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
15. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
16. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
17. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
18. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
19. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
20. For the formation of spirocyclic systems using one or two RCM steps, see: Maier, M. E.; Bugl, M. Synlett 1998, 1390-1392; 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, 6061-6064; Holt, D. J.; Barker, W. D.; Jenkins, P. R.; Davies, D. L.; Garratt, S.; Fawcett, J.; Russell, D. R.; Ghosh, S. Angew. Chem. 1998, 110, 3486-3488; Angew. Chem., Int. Ed. Engl. 1998, 37, 3298-3300; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250; Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139-4142; Holt, D. J.; Barker, W. D.; Jenkins, P. R; Panda, J.; Ghosh, S. J. Org. Chem. 2000, 65, 482-493.
21. A ring opening/ring closing metathesis sequence was recently exploited for the synthesis of piperidine derivatives starting from cyclopentenes: Stragies, R.; Blechert, S. Tetrahedron 1999, 55, 8179-8188.