Epoxidation with Peroxy Acids
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1 Epoxidation with Peroxy Acids RC 3 R C more reactive more likely Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. rg. Chem. 2000, 65, Singleton, D. A.; Merrigan, S. R.; Liu, J.; ouk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
2 Epoxidation under Basic Conditions Me t-bu Triton B Me t-bu TF Triton B = benzyltrimethylammonium hydroxide in 2 trans-decalind half-chair h Me 1,3-diaxial interaction Grieco, P. A. et al. J. Am. Chem. Soc. 1977, 99, 5773.
3 Epoxidation of Allyl Alcohols enbest epoxidation transition metal-catalyzed epoxidation relative rate V(acac) 2 t-bu 1.00 >200 R V t-bu oveyda, A..; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.enbest,. B.; Wilson, R. A. I. J. Chem. Soc. 1957, Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
4 Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
5 Early Examples of Asymmetric Epoxidation of Allyl Alcohols Yamada, S. et al. J. Am. Chem. Soc. 1977, 99, Sharpless, K. B. et al. J. Am. Chem. Soc. 1977, 99, 1990.
6 Essence of Sharpless Asymmetric Epoxidation Et 2 C C 2 Et [] slow D-( )-diethyl tartrate (unnatural) R 2 R 1 [] R 2 R 1 R 3 R 3 R R 3 R 2 R 1 Ti(i-Pr) 4 t-bub C 2 Cl 2 R 3 R 2 R 1 [] fast Et 2 C [] R 3 R 2 R 1 3 R R C 2 Et L-(+)-diethyl tartrate (natural) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; jima, I. Ed.; Wiley-VC: New York; 2000.
7 Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, Sharpless, K. B., et al. J. Am. Chem. Soc. 1987, 109, Katsuki, T. In Comprehensive Asymmetric Synthesis, Vol II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto,., Eds.; Springer:Berlin; Bn Bn ClC 2 S 2 Bn Bn L-(+)-DET Sharpless epoxidation Bn ClC 2 S 2 Bn single isomer Bn D-( )-DET Bn ClC 2 S 2 Bn single isomer Kajimoto, T.; Wong, C.-. Tetrahedron Lett. 1995, 36, 8247.
8 Kinetic Resolution of Racemic Allylic Alcohols (+)-DIPT Ti(i-Pr) 4 C 2 Cl 2 20 ºC + (S) erythro 98 : 2 threo (+)-DIPT Ti(i-Pr) 4 + C 2 Cl 2 20 ºC k fast /k slow = 104 fast slow (R) erythro 38 : 62 threo Sharpless, K. B., et al. J. Am. Chem. Soc. 1981, 103, 6237.
9 Combination of asymmetric synthesis and kinetic resolution can deliver products with very high ee. Ti(i-Pr) 4 (1.1 equiv) t-bu (2.0 equiv) ( )-DIPT (1.3 equiv) major C 2 Cl 2 25 ºC 80 85% yield minor 0.5 h: 88% ee 1h: 94%ee 1.5 h: >99.3% ee Schreiber, S. L., et al. J. Am. Chem. Soc. 1987, 109, 1525.
10 k 1 k 2 k 3 k 4
11 Catalyst Structure and Proposed Loaded Catalyst R E R R Ti E Ti R R R t-bu R E R Ti E Ti E R t-bu Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113. Katsuki, T. In Comprehensive Asymmetric Synthesis, Vol II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto,., Eds.; Springer:Berlin; 1999.
12 Asymmetric Epoxidation of Unfunctionalized lefins (30 mol %) XNE, K 2 C 3 C 3 CN/dimethoxymethane 0.05 M Na 2 B of aqueous 94% yield Na 2 (EDTA) (4x10-4 M) solution 95.5% ee XNE =2KS 5 KS 4 K 2 S 4 Shi, Y. et al. J. Am. Chem. Soc. 1997, 119, Na 2 (EDTA) is used to prevent trace-metal-catalyzed peroxide decomposition.
13 S 5 S 3 dioxirane
14 Mn Salen-Catalyzed Asymmetric Epoxidation N Mn N t-bu Cl t-bu t-bu t-bu (5 mol %) NaCl (aq.) C 2 Cl 2 81% yield 92% ee Jacobsen, E. N. et al. J. Am. Chem. Soc. 1991, 113, Jacobsen, E. N. et al. J. Am. Chem. Soc. 1990, 112, Katsuki, T. et al. Tetrahedron Lett. 1990, 31, 7345.
15 Dihydroxylation with smium Tetroxide catalytic reaction Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, acceleration by tertiary amines Criegee, R.; Marchand, B.; Wannowius,. Liebigs Ann. Chem. 1942, 550, 99.
16 Asymmetric Dihydroxylation (AD) Me N Ac N (1.1 equiv) s 4 (1.1 equiv) toluene LiAl 4 Sharpless, K. B., et al. J. Am. Chem. Soc. 1980, 102, % yield 83.2% ee Me N N N (1 mol%) N K 2 s 2 () 4 (0.2 mol%) K 3 Fe(CN) 6 (3 equiv), K 2 C 3 (3 equiv) C 3 S 2 N 2 (1 equiv) N t-bu/ 2 2 N Me Sharpless, K. B., et al. J. rg. Chem. 1992, 57, >80% yield >99.5% ee
17 Catalytic Cycle R R + L R s R R R s + L organic L aqueous s 2 s Fe(CN) Fe(CN) 6
18 Two Proposed Mechanisms offmann, R., et al. J. Am. Chem. Soc. 1986, 108, Corey, E. J., et al. J. Am. Chem. Soc. 1996, 118, Sharpless, K. B., et al. J. Am. Chem. Soc. 1997, 119, ouk, K. N.; Sharpless, K. B.; Singleton, D. A., et al. J. Am. Chem. Soc. 1997, 119, 9907.
19 Click Chemistry: Diverse Chemical Function from a Few Good Reactions artmuth C. Kolb, M. G. Finn, and K. Barry Sharpless* Angew. Chem. Int. Ed. 2001, 40, Nature is a matchless creator of C C linkages and we propose leaving the tough job of C C bond synthesis as much as possible to her.
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