Synthesis of polypropionate motifs containing the anti-anti unit

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 7067-7071

  Mochirian, Philippe ^a   Cardinal David, Benoit ^a   Guérin, Brigitte ^a   Prévost, Michel ^a   Guindon, Yvan ^a,b  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; PROPIONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MUKAIYAMA REACTION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037163294     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01557-5     Document Type: Article

References (25)

1. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
2. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
3. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
4. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
5. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
6. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
7. Representative leading references. Allenylmetalations: (a) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825. Aldol: (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354; (c) Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003. Allylmetalations: Boronate (d) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem., Int. Ed. 1999, 38, 1652. Borane (e) Guo, J. S.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187. Silane (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572. Titanate (g) BouzBouz, S.; Popkin, M. E.; Cossy, J. Org. Lett. 2000, 2, 3449.
8. Guindon Y., Houde K., Prévost M., Cardinal-David B., Landry S.R., Daoust B., Bencheqroun M., Guérin B. J. Am. Chem. Soc. 123:2001;8496.
9. Guindon Y., Prévost M., Mochirian P., Guérin B. Org. Lett. 4:2002;1019.
10. Gennari, C. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, 1993; Vol. 2, Chapter 2.4, pp. 629-660.
11. Mahrwald R. Chem. Rev. 99:1999;1095.
12. Endocyclic effect: the chelation of Lewis acids between the oxygen of the stereogenic center and the carbonyl of the ester leading to the syn product with high stereocontrol. See (a) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701; (b) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528; (c) Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289; (d) Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554; (e) Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852. See also Ref. 2a.
13. Endocyclic effect: the chelation of Lewis acids between the oxygen of the stereogenic center and the carbonyl of the ester leading to the syn product with high stereocontrol. See (a) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701; (b) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528; (c) Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289; (d) Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554; (e) Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852. See also Ref. 2a.
14. Endocyclic effect: the chelation of Lewis acids between the oxygen of the stereogenic center and the carbonyl of the ester leading to the syn product with high stereocontrol. See (a) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701; (b) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528; (c) Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289; (d) Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554; (e) Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852. See also Ref. 2a.
15. Endocyclic effect: the chelation of Lewis acids between the oxygen of the stereogenic center and the carbonyl of the ester leading to the syn product with high stereocontrol. See (a) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701; (b) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528; (c) Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289; (d) Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554; (e) Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852. See also Ref. 2a.
16. Endocyclic effect: the chelation of Lewis acids between the oxygen of the stereogenic center and the carbonyl of the ester leading to the syn product with high stereocontrol. See (a) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701; (b) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528; (c) Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289; (d) Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554; (e) Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852. See also Ref. 2a.
17. Exocyclic effect: the chelation of Lewis acids with the oxygen of the stereogenic center α to the carbon-centered radical and another neighboring heteroatom to form a temporary ring adjacent to the radical center that contributes to an enhancement of anti selectivity. See: Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289. See also Ref. 2b.
18. Aldehyde 1 was prepared by transforming β-hydroxy ester 6 into benzyloxy ester 7, which was then reduced to benzyloxy alcohol 8 before undergoing oxidation (see Supplementary material).
19. Variable and unpredictable selectivity is observed for chelate-controlled carbonyl additions of anti aldehydes containing opposing stereocontrol elements at α- and β-positions. See: Evans, D. A.; Allison, B. D.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840.
20. The anti relationship between the α and β substituents should contribute toward mutually reinforcing π-facial selectivity in carbonyl nucleophilic addition, see: Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322.
21. 2BOTf, indicating that chelation did not occur at this site. See: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778.
22. Present studies on bidendate complexes are aimed at evaluating both the importance of steric effects and the nature of heteroatoms in the presence of metal (saturated: e.g. Ti, Sn; or unsatured: e.g. Mg, Zn).
23. 4 and phenylselanyl-enoxysilane, indicating that the Mukaiyama reaction can take place under chelation control using these reagents.
24. 1H NMR analysis of the coupling constants of corresponding lactones 5a-d that were obtained by removal of the benzyl groups via catalytic hydrogenolysis. X-Ray structure was obtained for 5a.
25. A direct reduction could be achieved with the free hydroxy group in the absence of Lewis acid, but the results are more difficult to predict. This is due to intermolecular hydrogen bonding between the alcohol and the carbonyl and a subsequent competing endocyclic pathway. Alternatively, protection of the secondary alcohols by methyl ether should provide a 1:8 ratio (0°C) favoring the anti product as seen when an isopropyl is the substituent α to the alcohol. See Ref. 4d