Highly Selective Asymmetric Acetate Aldol Reactions of an N-Acetyl Thiazolidinethione Reagent

Organic Letters

Volumn 6, Issue 1, 2004, Pages 23-25

  Zhang, Yingchao ^a   Phillips, Andrew J ^a   Sammakia, Tarek ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; BORANE DERIVATIVE; LEUCINE; REAGENT; THIAZOLIDINE DERIVATIVE;

ALDOL REACTION; ARTICLE; STEREOCHEMISTRY;

ALDEHYDES; BORON COMPOUNDS; CHEMISTRY, ORGANIC; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; STEREOISOMERISM; THIAZOLES; VALINE;

EID: 0742304189     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036020y     Document Type: Article

References (44)

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2. For selected reviews on the aldol reaction, see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Arya, P.; Qin, H. P. Tetrahedron 2000, 56, 917. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (d) Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 39, 1353. (e) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed., Wiley: New York, 2000.
3. For selected reviews on the aldol reaction, see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Arya, P.; Qin, H. P. Tetrahedron 2000, 56, 917. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (d) Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 39, 1353. (e) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed., Wiley: New York, 2000.
4. For selected reviews on the aldol reaction, see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Arya, P.; Qin, H. P. Tetrahedron 2000, 56, 917. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (d) Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 39, 1353. (e) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed., Wiley: New York, 2000.
5. For selected reviews on the aldol reaction, see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Arya, P.; Qin, H. P. Tetrahedron 2000, 56, 917. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (d) Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 39, 1353. (e) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed., Wiley: New York, 2000.
6. For selected reviews on the aldol reaction, see: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Arya, P.; Qin, H. P. Tetrahedron 2000, 56, 917. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (d) Machajewski, T. D.; Wong, C. H. Angew. Chem., Int. Ed. 2000, 39, 1353. (e) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed., Wiley: New York, 2000.
7. (a) For selected examples, see: Crmmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894 and references therein. Abiko, A. ; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127.
8. (a) For selected examples, see: Crmmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894 and references therein. Abiko, A. ; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127.
9. (a) For selected examples, see: Crmmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894 and references therein. Abiko, A. ; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127.
10. (a) For selected examples, see: Crmmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894 and references therein. Abiko, A. ; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127.
11. (b) For recent advances in asymmetric synthesis with chiral imide auxiliaries, see: Evans, D. A.; Shaw, J. T. Actualité Chim. 2003, 35.
12. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
13. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
14. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
15. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
16. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
17. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
18. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
19. For reviews of asymmetric acetate aldol reactions, see: (a) Masamune, S. ; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. M. Braun, Angew. Chem., Int. Ed. Engl. 1987, 26, 24. For selected recent references to other auxiliary-based asymmetric acetate aldol reactions, see: (b) Oppolzer, W.; Starkemann, C. Tetrahedron Lett. 1992, 33, 2439. (c) Helmchen, G.; Leikauf, U.; Taufer-Knöpfel, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 874. (d) Bond, S.; Perlmutter, P. J. Org. Chem. 1997, 62, 6397. (e) Palomo, C.; Gonzalez, A.; Garcia, J. M.; Landa, C.; Oliarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. 1998, 37, 180. For approaches utilizing metal-based chirality, see: (f) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (g) Duthaler, R. O.; Herold, P.; Lottenbach, W.; Oertle, K.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 495. (h) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
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30. Dibutylboryl enolate of Evans' valine-derived oxazolidinone gives a 52: 48 ratio of diastereoisomers with isobutyraldehyde and a 72:28 ratio with acetaldehyde (see ref 1).
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32. For aldol reactions using dichlorophenylborane as the Lewis acid, see: (a) Hamana, H.; Sasakura, K.; Sugasawa, T. Chem. Lett. 1984, 1729. (b) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (c) Evans, D. A.; Fitch, D. M. J. Org. Chem. 1997, 62, 454. (d) Luke, G. P.; Morris, J. J. Org. Chem. 1995, 60, 3013.
33. For aldol reactions using dichlorophenylborane as the Lewis acid, see: (a) Hamana, H.; Sasakura, K.; Sugasawa, T. Chem. Lett. 1984, 1729. (b) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871. (c) Evans, D. A.; Fitch, D. M. J. Org. Chem. 1997, 62, 454. (d) Luke, G. P.; Morris, J. J. Org. Chem. 1995, 60, 3013.
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35. 3.
36. Auxiliary 3 has been synthesized from tert-leucinol on a 10 g scale by a modification of a general two-step literature procedure for the synthesis of thiazolidinethiones. Slightly harsher conditions are required for the synthesis of 3 than is typically required for other thiazolidinethiones due to the greater steric bulk of the tert-butyl group. See Supporting Information for details, (a) McKennon, M. J.; Meyers, A. I. J. Org. Chem. 1993, 58, 3568. (b) Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604.
37. Auxiliary 3 has been synthesized from tert-leucinol on a 10 g scale by a modification of a general two-step literature procedure for the synthesis of thiazolidinethiones. Slightly harsher conditions are required for the synthesis of 3 than is typically required for other thiazolidinethiones due to the greater steric bulk of the tert-butyl group. See Supporting Information for details, (a) McKennon, M. J.; Meyers, A. I. J. Org. Chem. 1993, 58, 3568. (b) Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604.
38. 4 and sparteine) gave lower diastereoselectivities (drs range from 2:1 to 6:1 for a variety of aldehydes). Enolization with other trialkylamine bases (Hunig's base or triethylamine) provided lower yields.
39. 3. We find that a 2:1 ratio of sparteine to compound 3 provides 92% enolization and that lower ratios of sparteine to 3 provide less enolization (1.5:1, 80% enolization; 1.2:1, 60% enolization).
40. Use of neutral silica gel (we used Mallinckrodt Silica Silica Gel 150, 60-200 mesh (75-250 μm), pH of a 5% slurry = 7.0) is crucial to the success of the purification procedure. Other typical "flash" silica gels we used provide cleavage of the auxiliary and lower yields. The addition of triethylamine to the solvent system is not beneficial and leads to cleavage of the auxiliary.
41. D = -8.4 (c 3.6, MeOH). See: Nelson, S. G.; Spencer, K. L. J. Org. Chem. 2000, 65, 1227.
42. Evans, D. A. In Proceedings of The Robert A. Welch Foundation Conferences on Chemical Research. XXXVII. Stereospecificity in Chemistry and Biochemistry; Nov. 7-9. 1983, Houston, TX; p 13.
43. (a) Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775.
44. (b) Cosp, A.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4629.