Diastereoselectivity in scalemic tartrate/titanium epoxidations

Chirality

Volumn 12, Issue 5-6, 2000, Pages 496-504

  Brown, John M ^a   Leppard, Simon J ^a   Oakes, John ^b   Thornthwaite, David ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

Bimetallic reagents; Diastereoselectivity; Epoxidation; Mechanism; Nonlinear effect

Indexed keywords

TARTARIC ACID DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; EPOXIDATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0034119136     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<496::aid-chir35>3.0.co;2-y     Document Type: Article

References (40)

1. Katsuki T, Sharpless KB. The first practical method for asymmetric epoxidation. J Am Chem Soc 1980;102:5974-5976; Dryzuk VG, Kartsev VG. Mechanism of the directing influence of functional groups and the geometry of reactant molecules on peroxide epoxidation of alkenes. Russ Chem Rev 1999;68:183-201.
2. Katsuki T, Sharpless KB. The first practical method for asymmetric epoxidation. J Am Chem Soc 1980;102:5974-5976; Dryzuk VG, Kartsev VG. Mechanism of the directing influence of functional groups and the geometry of reactant molecules on peroxide epoxidation of alkenes. Russ Chem Rev 1999;68:183-201.
3. Hanson RM, Sharpless KB. Procedure for the catalytic asymmetric epoxidation of allylic alcohols in the presence of molecular-sieves. J Org Chem 1986;51:1922-1925.
4. Martin VS, Woodard SS, Katsuki T, Yamada Y, Ikeda M, Sharpless KB. Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation - a route to substances of absolute enantiomeric purity. J Am Chem Soc 1981;103:6237-6240; McKee BH, Kalantar TH, Sharpless KB. Subtle effects in the asymmetric epoxidation: dependence of kinetic resolution efficiency on the monodentate alkoxide ligands of the bystander titanium center. J Org Chem 1991;56:6966-6968.
5. Martin VS, Woodard SS, Katsuki T, Yamada Y, Ikeda M, Sharpless KB. Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation - a route to substances of absolute enantiomeric purity. J Am Chem Soc 1981;103:6237-6240; McKee BH, Kalantar TH, Sharpless KB. Subtle effects in the asymmetric epoxidation: dependence of kinetic resolution efficiency on the monodentate alkoxide ligands of the bystander titanium center. J Org Chem 1991;56:6966-6968.
6. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
7. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
8. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
9. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
10. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
11. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
12. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
13. Guillaneux D, Zhao SH, Samuel O, Rainford D, Kagan HB. Nonlinear effects in asymmetric catalysis. J Am Chem Soc 1994;116:9430-9439; Puchot C, Samuel O, Dunach K, Zhao S, Agami C, Kagan HB. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. J Am Chem Soc 1986;108:2353-2357; Brunel JM, Luukas TO, Kagan HB. Nonlinear effects as 'indicators' in the tuning of asymmetric catalysts. Tetrahedron Asymmetry 1998;9: 1941-1946; Kagan HB, Girard C, Guillaneux D, Rainford D, Samuel O, Zhang SY, Zhao SH. Nonlinear effects in asymmetric catalysis - some recent aspects. Acta Chem Scand 1996;50:345-352; Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. Nonlinear stereochemical effects in asymmetric reactions. Tetrahedron: Asymmetry 1997;8:2997-3017; Blackmond DG. Kinetic implications of nonlinear effects in asymmetric synthesis. J Am Chem Soc 1998;120:13349-13353; Girard C, Kagan HB. Nonlinear effects in asymmetric synthesis and stereoselective reactions: ten years of investigation. Angew Chem Int Ed Engl 1998;37: 2923-2959; Kagan HB, Fenwick DR, Asymmetric amplification. Top Stereochem 1999;22:157-296.
14. Potvin PG, Bianchet S. The nature of the Katsuki-Sharpless asymmetric epoxidation catalyst. J Org Chem 1992;57:6629-6635; Lu LDL, Johnson RA, Finn MG, Sharpless KB. Two new asymmetric epoxidation catalysts - unusual stoichiometry and inverse enantiofacial selection. J Org Chem 1984;49:728-731.
15. Potvin PG, Bianchet S. The nature of the Katsuki-Sharpless asymmetric epoxidation catalyst. J Org Chem 1992;57:6629-6635; Lu LDL, Johnson RA, Finn MG, Sharpless KB. Two new asymmetric epoxidation catalysts - unusual stoichiometry and inverse enantiofacial selection. J Org Chem 1984;49:728-731.
16. Rossiter BE, Sharpless KB. Asymmetric epoxidation of homoallylic alcohols - synthesis of (-)-gamma-amino-βR-hydroxybutyric acid (Gabob). J Org Chem 1984;49:3707-3711.
17. Sharpless KB. The discovery of the asymmetric epoxidation. Chem Br 22:38 et seq., 1986; Sharpless KB. The discovery of titanium-catalyzed asymmetric epoxidation. Chemtech 1985;15:692-700; Sharpless KB, Woodard SS, Finn MG. On the mechanism of titanium-tartrate catalyzed asymmetric epoxidation. Pure Appl Chem 1983;55:1823-1836.
18. Sharpless KB. The discovery of the asymmetric epoxidation. Chem Br 22:38 et seq., 1986; Sharpless KB. The discovery of titanium-catalyzed asymmetric epoxidation. Chemtech 1985;15:692-700; Sharpless KB, Woodard SS, Finn MG. On the mechanism of titanium-tartrate catalyzed asymmetric epoxidation. Pure Appl Chem 1983;55:1823-1836.
19. Sharpless KB. The discovery of the asymmetric epoxidation. Chem Br 22:38 et seq., 1986; Sharpless KB. The discovery of titanium-catalyzed asymmetric epoxidation. Chemtech 1985;15:692-700; Sharpless KB, Woodard SS, Finn MG. On the mechanism of titanium-tartrate catalyzed asymmetric epoxidation. Pure Appl Chem 1983;55:1823-1836.
20. Williams ID, Pedersen SF, Sharpless KB, Lippard SJ. Crystal-structures of 2 titanium tartrate asymmetric epoxidation catalysts. J Am Chem Soc 1984;106:6430-6431; Pedersen SF, Dewan JC, Eckman RR, Sharpless KB. Unexpected diversity in the coordination chemistry of tartrate esters with titanium (IV). J Am Chem Soc 1987;109:1279-1282.
21. Williams ID, Pedersen SF, Sharpless KB, Lippard SJ. Crystal-structures of 2 titanium tartrate asymmetric epoxidation catalysts. J Am Chem Soc 1984;106:6430-6431; Pedersen SF, Dewan JC, Eckman RR, Sharpless KB. Unexpected diversity in the coordination chemistry of tartrate esters with titanium (IV). J Am Chem Soc 1987;109:1279-1282.
22. Corey EJ. On the origin of enantioselectivity in the Katsuki-Sharpless epoxidation procedure. J Org Chem 1990;55:1693-1694.
23. Finn MG, Sharpless KB. Mechanism of asymmetric epoxidation. 2. Catalyst structure. J Am Chem Soc 1991;113:113-126; Woodard SS, Finn MG, Sharpless KB. Mechanism of asymmetric epoxidation. 1. Kinetics. J Am Chem Soc 1991;113:106-113.
24. Finn MG, Sharpless KB. Mechanism of asymmetric epoxidation. 2. Catalyst structure. J Am Chem Soc 1991;113:113-126; Woodard SS, Finn MG, Sharpless KB. Mechanism of asymmetric epoxidation. 1. Kinetics. J Am Chem Soc 1991;113:106-113.
25. Wu Y-D, Lai DKW. A density functional study on the stereocontrol of the Sharpless epoxidation. J Am Chem Soc 1995;117:11327-11336; Wu Y-D, Lai DKW. Transition structure for the epoxidation mediated by titanium (IV) peroxide. A density functional study. J Org Chem 1995; 60:673-680.
26. Wu Y-D, Lai DKW. A density functional study on the stereocontrol of the Sharpless epoxidation. J Am Chem Soc 1995;117:11327-11336; Wu Y-D, Lai DKW. Transition structure for the epoxidation mediated by titanium (IV) peroxide. A density functional study. J Org Chem 1995; 60:673-680.
27. Ismagilov RF. Mathematical description of kinetic resolution with an enantiomerically impure catalyst and nonracemic substrate. J Org Chem 1998;63:3772-3774; Johnson DW, Singleton DA. Nonlinear effects in kinetic resolutions. J Am Chem Soc 1999;121:9307-9312; Luukas TO, Girard C, Fenwick DR, Kagan HB. Kinetic resolution when the chiral auxiliary is not enantiomerically pure: normal and abnormal behavior. J Am Chem Soc 1999:9299-9306.
28. Ismagilov RF. Mathematical description of kinetic resolution with an enantiomerically impure catalyst and nonracemic substrate. J Org Chem 1998;63:3772-3774; Johnson DW, Singleton DA. Nonlinear effects in kinetic resolutions. J Am Chem Soc 1999;121:9307-9312; Luukas TO, Girard C, Fenwick DR, Kagan HB. Kinetic resolution when the chiral auxiliary is not enantiomerically pure: normal and abnormal behavior. J Am Chem Soc 1999:9299-9306.
29. Ismagilov RF. Mathematical description of kinetic resolution with an enantiomerically impure catalyst and nonracemic substrate. J Org Chem 1998;63:3772-3774; Johnson DW, Singleton DA. Nonlinear effects in kinetic resolutions. J Am Chem Soc 1999;121:9307-9312; Luukas TO, Girard C, Fenwick DR, Kagan HB. Kinetic resolution when the chiral auxiliary is not enantiomerically pure: normal and abnormal behavior. J Am Chem Soc 1999:9299-9306.
30. Woodard SS, Ph.D. dissertation, Department of Chemistry, Stanford University, 1981; Finn MG, Ph.D. dissertation, Department of Chemistry, MIT, 1986.
31. Woodard SS, Ph.D. dissertation, Department of Chemistry, Stanford University, 1981; Finn MG, Ph.D. dissertation, Department of Chemistry, MIT, 1986.
32. Midland MM, Tramontano A, Kazubski A, Graham RS, Tsai DJS, Cardin DB. Asymmetric reductions of propargyl ketones. An effective approach to the synthesis of optically active compounds. Tetrahedron 1984;40:1371-1380.
33. Katsuki T, Lee AWM, Ma P, Martin VS, Masamune S, Sharpless KB, Tuddenham D, Walker FJ. Synthesis of saccharides and related polyhydroxylated natural products. 1. Simple alditols. J Org Chem 1982; 47:1373-1378.
34. Schmid CR, Bryant JD, Dowlatzedah M, Phillips JL, Prather DE, Schantz RD, Sear NL, Vianco CS. Synthesis of 2,3-O-isopropylidene-D-glyceraldehyde in high chemical and optical purity: observations on the development of a practical bulk process. J Org Chem 1991;56: 4056-4058.
35. Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB. Catalytic asymmetric epoxidation and kinetic resolution - modified procedures including in situ derivatization. J Am Chem Soc 1987;109: 5765-5780; Sharpless and co-workers report a previous kinetic resolution in epoxidation of alcohol 1: McKee BH, Kalantar TH, Sharpless KB. Subtle effects in the asymmetric epoxidation - dependence of kinetic resolution efficiency on the monodentate alkoxide ligands of the bystander titanium center. J Org Chem 1991;56:6966-6968.
36. Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB. Catalytic asymmetric epoxidation and kinetic resolution - modified procedures including in situ derivatization. J Am Chem Soc 1987;109: 5765-5780; Sharpless and co-workers report a previous kinetic resolution in epoxidation of alcohol 1: McKee BH, Kalantar TH, Sharpless KB. Subtle effects in the asymmetric epoxidation - dependence of kinetic resolution efficiency on the monodentate alkoxide ligands of the bystander titanium center. J Org Chem 1991;56:6966-6968.
37. Perrin DD. Purification of laboratory chemicals. Oxford: Pergamon; 1988.
38. Baker KV, Brown JM, Hughes N, Skarnulis AJ, Sexton A Mechanical activation of magnesium turnings for the preparation of reactive Grignard-reagents. J Org Chem 1991;56:698-703.
39. Brown JM, Leppard SW, Lloyd-Jones GC. A rapid assay for the enantiomeric purity of secondary alcohols using 4S,5R-4-methyl,5-phenyl-1,3,2-oxazaborolidine (Ephedrineborane). Tetrahedron: Asymmetry 1992;3:261-266.
40. Trippett S, Walker DM. The chemistry of phosphobetaines: synthesis and reactivity. J Chem Soc 1961:1266.