Lewis acid-mediated addition of silylated methylenecyclopropane to aldehydes - Synthesis of tetrahydrofuran derivatives

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 1015-1017

  Patient, Lee ^a   Berry, Malcolm B ^b   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Lewis acid; Methylenecyclopropane; Tetrahydrofuran

Indexed keywords

ALDEHYDE DERIVATIVE; CYCLOPROPANE DERIVATIVE; LEWIS ACID; METHYLENECYCLOPROPANE; NAPHTHALENE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; SILYLATION; SYNTHESIS;

EID: 0037467826     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02737-5     Document Type: Article

References (20)

1. Binger, P.; Schmidt, T. Houben-Weyl, A. de Meijere, Ed., Thieme: Stuttgart, 1997, E17c, 2217-2294.
2. See for example: (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77-151; (b) Corlay, H.; Lewis, R. T.; Motherwell, W. T.; Shipman, M. Tetrahedron 1995, 51, 3303-3318; (c) Lewis, R. T.; Motherwell, W. B.; Shipman, M.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1995, 51, 3289-3302.
3. See for example: (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77-151; (b) Corlay, H.; Lewis, R. T.; Motherwell, W. T.; Shipman, M. Tetrahedron 1995, 51, 3303-3318; (c) Lewis, R. T.; Motherwell, W. B.; Shipman, M.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1995, 51, 3289-3302.
4. See for example: (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77-151; (b) Corlay, H.; Lewis, R. T.; Motherwell, W. T.; Shipman, M. Tetrahedron 1995, 51, 3303-3318; (c) Lewis, R. T.; Motherwell, W. B.; Shipman, M.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1995, 51, 3289-3302.
5. Huval C.C., Singleton D.A. Tetrahedron Lett. 35:1994;689-690.
6. See for example: (a) Watson, F. C.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10341-10345; (b) Boffey, R. J.; Whittingham, W. G.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2001, 487-496; (c) Pike, K. G.; Destabel, C.; Anson, M.; Kilburn, J. D. Tetrahedron Lett. 1998, 39, 5877-5880; (d) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365-1368.
7. See for example: (a) Watson, F. C.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10341-10345; (b) Boffey, R. J.; Whittingham, W. G.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2001, 487-496; (c) Pike, K. G.; Destabel, C.; Anson, M.; Kilburn, J. D. Tetrahedron Lett. 1998, 39, 5877-5880; (d) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365-1368.
8. See for example: (a) Watson, F. C.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10341-10345; (b) Boffey, R. J.; Whittingham, W. G.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2001, 487-496; (c) Pike, K. G.; Destabel, C.; Anson, M.; Kilburn, J. D. Tetrahedron Lett. 1998, 39, 5877-5880; (d) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365-1368.
9. See for example: (a) Watson, F. C.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10341-10345; (b) Boffey, R. J.; Whittingham, W. G.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2001, 487-496; (c) Pike, K. G.; Destabel, C.; Anson, M.; Kilburn, J. D. Tetrahedron Lett. 1998, 39, 5877-5880; (d) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365-1368.
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14. 4 which yielded a regioisomeric mixture of chloroalkenols: see Ref. 5.
15. Palladium-catalysed [3+2] cycloadditions of alkylidenecyclopropanes with aldehydes have recently been described: Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298-1300. Thermal [3+2] cycloadditions of alkylidenecyclopropane acetals with carbonyl compounds have also been described: Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553-5555.
16. Palladium-catalysed [3+2] cycloadditions of alkylidenecyclopropanes with aldehydes have recently been described: Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298-1300. Thermal [3+2] cycloadditions of alkylidenecyclopropane acetals with carbonyl compounds have also been described: Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553-5555.
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18. 4 derivatives.
19. 4 derivatives.
20. 1,2-Silyl shifts of the trisisopropylsilyl group are well precedented: Knölker H.-J. J. Prakt. Chem. 339:1997;304-314.