Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3973-3975

  Bartoli, Giuseppe ^a   Bosco, Marcella ^a   Carlone, Armando ^a   Locatelli, Manuela ^a   Melchiorre, Paolo ^a   Sambri, Letizia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; KINETICS; ROOM TEMPERATURE;

EID: 8744264856     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048322l     Document Type: Article

References (25)

1. (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
2. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
3. (c) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; p 243.
4. While chiral 2-amino-1-ols are readily accessible by reduction of α-amino acids, asymmetric routes to 1,2-amino alcohols with a stereogenic hydroxy-substituted carbon center are relatively uncommon. For some leading references, see: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. (c) Effenberger, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1515. (d) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510. (e) Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 42, 4241.
5. While chiral 2-amino-1-ols are readily accessible by reduction of α-amino acids, asymmetric routes to 1,2-amino alcohols with a stereogenic hydroxy-substituted carbon center are relatively uncommon. For some leading references, see: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. (c) Effenberger, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1515. (d) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510. (e) Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 42, 4241.
6. While chiral 2-amino-1-ols are readily accessible by reduction of α-amino acids, asymmetric routes to 1,2-amino alcohols with a stereogenic hydroxy-substituted carbon center are relatively uncommon. For some leading references, see: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. (c) Effenberger, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1515. (d) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510. (e) Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 42, 4241.
7. While chiral 2-amino-1-ols are readily accessible by reduction of α-amino acids, asymmetric routes to 1,2-amino alcohols with a stereogenic hydroxy-substituted carbon center are relatively uncommon. For some leading references, see: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. (c) Effenberger, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1515. (d) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510. (e) Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 42, 4241.
8. While chiral 2-amino-1-ols are readily accessible by reduction of α-amino acids, asymmetric routes to 1,2-amino alcohols with a stereogenic hydroxy-substituted carbon center are relatively uncommon. For some leading references, see: (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451. (b) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. (c) Effenberger, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1515. (d) Ohkuma, T.; Ishii, D.; Takeno, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 6510. (e) Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 42, 4241.
9. (a) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
10. Review: (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
11. For carbamate-based aminohydroxylation of olefins, see: Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813.
12. During the manuscript preparation, an interesting opening of enantiopure terminal epoxides with N-Boc-2-nitrobenzenesulfonamide was reported: Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952.
13. Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Massaccesi, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 6, 2173.
14. (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
15. (b) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.
16. See footnote 24 in ref 7b. See also ref 15.
17. Small amounts of 1,2-diol and p-nitrobenzoate addition product were also generated, presumably as a result of adventitious water and counterion addition. For the latter path, see: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773. The use of molecular sieves to inhibit diol production had no significant effects.
18. The selectivity factors s were calculated using the equation s = ln[1 - c(1 + ee)]/ln[1 - c(1 - ee)], where ee is the enantiomeric excess of the amino alcohol product and c is the conversion (set to equal the isolated yield). Given the high selectivity of AKR (s > 400), the absolute magnitudes of s factors are certainly lacking precision; see the Supporting Information for details.
19. Klunder J. M.; Ko, S. Y.; Sharpless, K. B. J. Org. Chem. 1986, 51, 3710.
20. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086. See also ref 3a.
21. For a recent example, see: Nesterenko, V.; Putt, K. S.; Hergenrother, P. J. J. Am. Chem. Soc. 2003, 125, 14672.
22. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207. See also ref 13.
23. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360. See also ref 12.
24. Also the unreacted epoxides can be recovered in high ee (> 90%).
25. For practical considerations on kinetic resolution strategy, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth., Catal. 2001, 343, 5.