Asymmetric synthesis of conformationally constrained cis-1-amino-1-phenylcyclohexan-2-ol

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1501-1506

  Senanayake, Chris H ^a,b   Larsen, Robert D ^a   DiMichele, Lisa M ^a   Liu, Ji ^a   Toma, Pascal H ^a   Ball, Richard G ^a   Verhoeven, Thomas R ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b SUNOVION PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 1 PHENYL 2 CYCLOHEXANOL; CYCLOHEXANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030014624     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00169-3     Document Type: Article

References (25)

1. (a) Senanayake, C. H.; Roberts, F. E.; DiMichele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 3993.
2. (b) Senanayake, C. H.; DiMichele, L. M.; Liu, J.; Fredenburgh, L. E.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7615.
3. 2-symmetric bis(oxazolines), see: Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 813
4. (a) Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619.
5. (b) Ghosh, A. K.; Chen, Y. Tetrahedron Letters 1995, 36, 6811.
6. (c) Gao, Y.; Hong, Y.; Nie, X.; Zepp, M. C. Tetrahedron Lett. 1994, 35, 673.
7. (d) Askin, D.; Eng, K. K.; Rossen, K.; Purick, R. M.; Wells, R. P.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1994, 35, 673.
8. (e) Armstrong, J. D.; Hartner, F.W.; DeCamp, A.E.; Volante, R.P.; Shinkai, I. Tetrahedron Lett. 1992, 33, 6599.
9. 2-symmetric bis(oxazolines) in two-point binding asymmetric Diels-Alder reactions. Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. in press.
10. Vanrheenen, V.; Kelly, R.C.; Cha, D.Y. Tetrahedron Lett. 1976, 1973
11. For a racemic synthesis of cis-1-amino-1-phenylcyclohexan-2-ol, see: Stevens, C. L.; Ash, A. B.; Thuillier, A.; Amin, J. H.; Balys. A.; Dennis, W. E.; Dickerson, J. P.; Glinski. R. P.; Hanson, H. T.; Pillai, D. M.; Stoddard, J. W. J. Org. Chem. 1966, 32, 2593.
12. Sharpless, B. K.; King, S. B. Tetrahedren Lett. 1994, 35, 5611, and references cited therein.
13. (a) Crystallographic-quality crystals of compound 1 were grown by slow evaporation of an ethanol solution.
14. (b) Sheldrick, G.M., Acta Crystallogr. 1990, A46, 467.
15. (c) Structure Determination Package Version 3, Enraf-Nonius, Delft, 1985.
16. (d) Compound 1 exists as two conformational isomers at low temperature (T=-40°C to -60°C). The proton and carbon-13 data presented in this paper are derived from room temperature spectra and represent the average chemical shifts and coupling constants for both isomers.
17. Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378.
18. (a) Jacobsens's AE with S,S manganese salen catalyst provides the same sense of induction for compound 1 as Sharpless' AD-mix-β catalyst.
19. 15ON: C, 78.84; H, 7.08; N, 6.56. Found: C, 78.80; H, 7.01; N, 6.25.
20. These types of ligands are becoming extremely valuable in metal-catalyzed asymmetric reactions. For pioneering work in this area, see: (a) Blom, C.; Weickhardt, K. Helv. Chim. Acta 1991, 74, 717.
21. (b) Blom, C.; Weickhardt, K.; Ranff, T. Chem. Ber. 1991, 124, 1173.
22. (c) Blom, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848.
23. (d) Serrano, J. L.; Sierra, T.; Gonzalez, Y.; Bolm, C.; Weickhardt, K.; Magnus, A.; Moll, G. J. Am. Chem. Soc. 1995, 117, 8312, and references cited therein.
24. The curved arrows represent observed NOEs, and the values have been corrected for residual magnetization. The relative stereochemistry of compound 8 was unambiguously established as cis by acid hydrolysis to the known amino alcohol 1.
25. 1b to provide ligand 9a and 9b respectively, by using the identical procedure as described in the experimental procedure for ligand 8. formula presented