Enantioselective hydrolysis of N-acylated α-amino esters at a biphasic interface: Tandem reaction kinetic resolution using a chiral complexing agent

Organic Letters

Volumn 4, Issue 19, 2002, Pages 3283-3286

  Snyder, Seth E ^a   Pirkle, William H ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

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ARTICLE;

EID: 0012476323     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026517s     Document Type: Article

References (22)

1. For a review, see: Dalko P. I.; Moisan L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
2. For pertinent reviews on kinetic resolution, see: (a) Keith J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26.
3. (b) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
4. Miller, S. J.; Copeland, G. T.; Papaioaaou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629-1630.
5. Chen, Y.; Tian, S.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542-9543.
6. (a) Oriyama, T.; Hori, Y.; Imai, K.; Sasaki, R. Tetrahedron Lett. 1996, 37, 8543-8546.
7. (b) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265-266.
8. Sellergren, B.; Shea, K. J. Tetrahedron: Asymmetry 1994, 5, 1403-1406.
9. For relevant articles dealing with enantioselective ester hydrolysis at a micellar interface, see: (a) Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1994, 59, 4194-4201.
10. (b) Cleij, M. C.; Scrimin, P.; Tecilla, P.; Tonellato, U. Langmuir 1996, 12, 2596-2560.
11. (c) Cleij, M. C.; Drenth, W.; Nolte, R. J. M. J. Org. Chem. 1991, 56, 3883-3891.
12. For the biphasic kinetic resolution of racemic aldols using aldolase antibodies, see: Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem. Eur. J. 2000, 6, 2772-2774.
13. Pirkle, W. H.; Snyder, S. E. Org. Lett. 2001, 3, 1821-1823.
14. For preparation of racemates used in this study, see: (a) Pirkle, W. H.; Hyun, M. H.; Bank, B. J. Chromatogr. 1984, 316, 585-604.
15. (b) Pirkle, W. H.; Pochapsky, T. C.; Mahler, G. S.; Field, R. M. J. Chromatogr. 1985, 348, 89-96.
16. (c) Pirkle, W. H.; Burke, J. A., III. J. Chromatogr. 1991, 557, 173-185.
17. For preparation of (S)-4. see: Pirkle, W. H.; Koscho, M. E. J. Chromatogr. A 1999, 840, 151-158.
18. iPrOH in hexane)).
19. For a recent article dealing with control over regioselectivity by orientation at interfaces, see: Buijnsters P. J. J. A.; Feiters, M. C.; Nolte, R. J. M.; Sommerdijk, N. A. J. M.; Zwanenburg, B. Chem. Commun. 2001, 269-270.
20. Isolation of products from the hydrolysis of the dimethyl esters of glutamic and aspartic acid reveals that both methyl groups are cleaved.
21. Typical Procedure for Tandem Esterification/Hydrolysis Reaction. A solution of phenacyl bromide (0.05 mmol), (S)-4 (0.10 mmol), and tetrahexylammonium bromide (0.003 mmol) in 2.75 mL of carbon tetrachloride and 0.10 mL of methylyne chloride was stirred with a solution of N-3,5-dinitrobenzoyl leucine (0.10 mmol) in 1.25 mL of saturated sodium bicarbonate for 27 h. At this point, 1.25 mL of 2 M NaOH was added, and the reaction mixture was stirred for an additional 4 h. The layers were separated and worked up as described in ref 12.
22. Immediately following the addition of 2 M sodium hydroxide, the organic layer turns dark purple. The color disappears following acidic workup. The effect is attributed to the formation of a transient Meisenheimer complex stabilized by the quaternary ammonium cation. This secondary process is currently under investigation.