Asymmetric aminohydroxylation of substituted styrenes using t-butyl carbamate

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 4099-4102

  O'Brien, Peter ^a   Osborne, Simon A ^b   Parker, Daniel D ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CARBAMIC ACID; DIAMINE; LIGAND; STYRENE; TERT BUTYLCARBAMATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROXYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032482497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00665-0     Document Type: Article

References (24)

1. 1. O'Brien, P.; Poumellec, P. Tetrahedron Lett., 1996, 37, 5619-5622.
2. 2. de Sousa, S. E.; O'Brien, P. Tetrahedron Lett., 1997, 38, 4885-4888.
3. 3. de Sousa, S. E.; O'Brien, P.; Poumellec, P. Tetrahedron: Asymmetry, 1997, 8, 2613-2618.
4. 4. O'Brien, P.; Poumellec, P. Tetrahedron Lett., 1996, 37, 8057-8058.
5. 5. Styrene oxide (Aldrich Chemical Company) and phenylglycinol (Lancaster Synthesis) are available.
6. 6. Koga has described the use of diamines 4 with aromatic groups other than phenyl in the asymmetric deprotonation of 4-substituted cyclohexanones but he did not comment on how they were prepared: Toriyama, M.; Sugasawa, K.; Shindo, M.; Tokutake, N.; Koga, K. Tetrahedron Lett., 1997, 38, 567-570.
7. 7. Rossiter has reported an asymmetric dihydroxylation route to diamines 4 with non-phenyl aromatic groups: Miao, G.; Rossiter, B. E. J. Org. Chem., 1995, 60, 8424-8427.
8. 8. Li, G.; Chang, H-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl., 1996, 35, 451-454; Li, G., Sharpless, K. B. Acta Chem. Scand., 1996, 50, 649-651.
9. 8. Li, G.; Chang, H-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl., 1996, 35, 451-454; Li, G., Sharpless, K. B. Acta Chem. Scand., 1996, 50, 649-651.
10. 9. Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl., 1996, 35, 2813-2817.
11. 10. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc., 1998, 120, 1207-1217.
12. 11. Rudolph, J.; Sennhenn, P.C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl., 1996, 35, 2810-2813.
13. 12. For useful applications of asymmetric aminohydroxylation in synthesis, see: Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett., 1997, 38, 1407-1410; Upadhya, T. T.; Sudalai, A. Tetrahedron: Asymmetry, 1997, 8, 3685-3689.
14. 12. For useful applications of asymmetric aminohydroxylation in synthesis, see: Angelaud, R.; Landais, Y.; Schenk, K. Tetrahedron Lett., 1997, 38, 1407-1410; Upadhya, T. T.; Sudalai, A. Tetrahedron: Asymmetry, 1997, 8, 3685-3689.
15. 13. For overview articles on asymmetric aminohydroxylation, see: Reiser, O. Angew. Chem., Int. Ed. Engl., 1996, 35, 1308-1309;
16. Casiraghi, G.; Rassu, G.; Zanardi, F. Chemtracts-organic, 1997, 10, 318-321.
17. 14. Sharpless, K. B. personal communication: 2:1 n-propanol-water solvent system was recommended to us by Sharpless as he had observed significant levels of dihydroxylation with a greater proportion of water.
18. 15. By preparing authentic samples of (S)-9a and (S)-10a from (S)-phenylgrycinol, we were able to establish the sense of induction in the reactions with styrene 5 and the stereochemistries indicated in the remainder of this paper are assigned by analogy. They are consistent with those obtained by Sharpless (references 10 and 14).
19. 13C NMR spectroscopy, microanalysis and high resolution mass spectrometry.
20. -1.
21. 18. Chiral HPLC (Table 1 ): 9a, Chiralcel OJ; 10a and 16a. Regis (S,S) Whelk-O 1; 12a, Chiralcel OD-H; 13a and 15a, Chiralpak AD.
22. 19. Chiral HPLC (Table 2): 19a, Chiralcel OJ; 20a, Chiralcel OD-H.
23. 2PHAL.
24. 21. All of the amino alcohols in Table 2 have been converted into the corresponding arylglycinols.