Catalytic asymmetric synthesis of anti-1,2-diols [1]

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7386-7387

  Notz, Wolfgang ^a   List, Benjamin ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; NATURAL PRODUCT;

CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034596299     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001460v     Document Type: Letter

References (20)

1. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis, John Wiley & Sons: New York, 1989.
2. (a) Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1995, 34, 1059.
3. (b) Review: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 3-2547.
4. For alternative, indirect, and noncatalytic methods, see for example: (a) Enzymatic desymmetrization of 2,3-prolected meso-butane-1,2,3,4-tetrol derivatives: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769. (b) Enantioselective hydroxyallylation of aldehydes: Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563-7566. (c) Asymmetric epoxidation/Payne-rearrangement/epoxide-opening: i. Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264. (d) Enantioselective enzymatic hydrolysis of a racemic trans-epoxide: Weijers, C. A. G. M. Tetrahedron: Asymmetry 1997, 8, 639-647.
5. For alternative, indirect, and noncatalytic methods, see for example: (a) Enzymatic desymmetrization of 2,3-prolected meso-butane-1,2,3,4-tetrol derivatives: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769. (b) Enantioselective hydroxyallylation of aldehydes: Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563-7566. (c) Asymmetric epoxidation/Payne-rearrangement/epoxide-opening: i. Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264. (d) Enantioselective enzymatic hydrolysis of a racemic trans-epoxide: Weijers, C. A. G. M. Tetrahedron: Asymmetry 1997, 8, 639-647.
6. For alternative, indirect, and noncatalytic methods, see for example: (a) Enzymatic desymmetrization of 2,3-prolected meso-butane-1,2,3,4-tetrol derivatives: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769. (b) Enantioselective hydroxyallylation of aldehydes: Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563-7566. (c) Asymmetric epoxidation/Payne-rearrangement/epoxide-opening: i. Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264. (d) Enantioselective enzymatic hydrolysis of a racemic trans-epoxide: Weijers, C. A. G. M. Tetrahedron: Asymmetry 1997, 8, 639-647.
7. For alternative, indirect, and noncatalytic methods, see for example: (a) Enzymatic desymmetrization of 2,3-prolected meso-butane-1,2,3,4-tetrol derivatives: Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769. (b) Enantioselective hydroxyallylation of aldehydes: Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563-7566. (c) Asymmetric epoxidation/Payne-rearrangement/epoxide-opening: i. Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264. (d) Enantioselective enzymatic hydrolysis of a racemic trans-epoxide: Weijers, C. A. G. M. Tetrahedron: Asymmetry 1997, 8, 639-647.
8. Mukaiyama, T.; Shiina, I.; Uchiro, H.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1994, 67, 1708-1716.
9. For excellent reviews on aldolases and the catalytic asymmetric aldol reaction in general, see: (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (b) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352-1374.
10. For excellent reviews on aldolases and the catalytic asymmetric aldol reaction in general, see: (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.- H. Chem. Rev. 1996, 96, 443-473. (b) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352-1374.
11. (a) List, B.; Shabat, D. Barbas, C. F., III; Lerner, R. A. Chem. Eur. J. 1998, 881-885.
12. (b) Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 1998, 120, 2768-2779.
13. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
14. Diastereoselectivities and enantioselectivities were determined by comparison with the syn-enantiomers obtained from the aldehydes via Horner-Wadsworth-Emmons-reaction followed by Sharpless asymmetric dihydroxylations using either AD-mix-α or AD-mix-β (Walsh, P. J.; Sharpless, K. B. Synlett 1993, 605-606). The proline catalyzed reactions were performed with both D- and L-proline so that all four stereoisomers were available. Finally, conditions for the separation of all four stereoisomers were established by using chiral-phase HPLC techniques.
15. Benzaldehyde gave similar results (dr = 1.3:1, ee = 80%).
16. Izquierdo Cubero, I.; Garcia Poza, D. Carbohydr. Res. 1985, 138, 139-42.
17. Lopez Aparicio, F. J.; Gomez Guillen, M.; Izquierdo Cubero, I. Ann. Quim. 1976, 72, 938-945.
18. Regio- and presumed (E)-slereoselectivity of the enamine formation may result from (a) conjugation (Lin, J.-F.; Wu, C.-C.; Lien, M.-H. J. Phys. Chem. 1995, 99, 16903-16908) and (b) minimization of 1,3-allylic strain (Hoffmann, R. W. Chem. Res. 1989, 89, 1841-1860). However, the enamine geometry may not necessarily be reflected in product diastereoselectivity, as in the case of kinetically controlled aldol reactions of preformed enolates; related transition states involving a (Z)-enamine can be constructed.
19. Regio- and presumed (E)-slereoselectivity of the enamine formation may result from (a) conjugation (Lin, J.-F.; Wu, C.-C.; Lien, M.-H. J. Phys. Chem. 1995, 99, 16903-16908) and (b) minimization of 1,3-allylic strain (Hoffmann, R. W. Chem. Res. 1989, 89, 1841-1860). However, the enamine geometry may not necessarily be reflected in product diastereoselectivity, as in the case of kinetically controlled aldol reactions of preformed enolates; related transition states involving a (Z)-enamine can be constructed.
20. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.