Scheme 1 Scheme 2 Chart 1 Scheme ( 44 )
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1 Catalytic Asymmetric Aldol Reactions in Aqueous Media Tomoaki Hamada, Kei Manabe, and Shu Kobayashi* Catalytic asymmetric aldol reactions in aqueous media have been developed using Pr(OTf)3 and chiral bis-pyridino-18-crown-6 1. In the asymmetric aldol reaction using rare earth metal triflates (RE(OTf3) and 1, slight changes in ionic diameters of the metal cations greatly affected the diastereo- and enantioselectivities of the products. It was found that the binding ability of the crown ether with the RE cation and the catalytic activity of the complex were important for achieving high selectivity in the asymmetric aldol reactions. In this reaction, water plays an essential role for the good yield and selectivities. Several aldehydes and silyl enol ethers derived from ketones and thioesters can be employed in the catalytic asymmetric aldol reactions using Pr(OTf)3 and 1 to provide the desired aldol adducts in good to high yields and stereoselectivities. Key words: catalytic asymmetric aldol reaction, aqueous media, chiral bis-pyridino-18-crown-6, rare earth metal triflate, ionic diameter, binding ability, catalytic activity, Pr(OTf )3, silyl enol ether, crown ether Graduate School of Pharmaceutical Sciences, The University of Tokyo Vol.61 No ( 43 ) 445
2 Scheme 1 Scheme 2 Chart 1 Scheme ( 44 )
3 Table 1 Effect of solvents. Fig 1 Enantio- and diastereoselectivities in the aldol reaction using rare earth metal triflates and 1, and ionic diameters (8-coordination for Sc, 9-coordination for other metals) of the metal cations (RE3+). Yields: 49-95% Vol.61 No ( 45 ) 447
4 Table 2 Binding constants of crown ethers (1, 3, or 4) with La3+ or Y3+. Fig 2 Enantio- and diastereoselectivities in the aldol reaction using rare earth metal triflates and 3. Yield: 30-89% Fig 3 Enantio- and diastereoselectivities in the aldol reaction using rare earth metal triflates and 4. Yield: 22-89%
5 Fig 4 Initial reaction rates of the asymmetric reactions. (open circle: Pr(OTf)3; closed circle: Pr(OTf)3+1; open square: Pr(OTf)3+3; closed square: Pr(OTf)3+4 Fig 5 [Pr(NO3)2 1]+ moiety in the X-ray structure of [Pr(NO3)2 1]3[Pr(NO3)6]. (a) Top view. (b) Side view. Hydrogen atoms are omitted for clarity. (c) ORTEP drawing of [Pr(NO3)2 E1]+Pr(NO3)6]3-. Vol.61 No ( 47 ) 449
6 (a) (b) (r) (d) (a) Fig 6 X-ray structures of complexes of 1. (a) [Ce(NO3)2 E1]+ moiety in the X-ray structure of [Ce(NO3)2 E1]3[Ce(NO3)6]. (b) [Gd(NO3)2 E1]+ moiety in the X-ray structure of [Gd(NO3)2 E1](NO3). (c) [Y(NO3)2 E1]+ moiety in the X-ray structure of [Y(NO3)2 E1](1N-03). (d) [Pr(NO3)2 E3]+ moiety in the X-ray structure of [Pr(NO3)2 E3]3[Pr(NO3)6]. (e) [Pr(NO3)2 E4]+ moiety in the X-ray structure of [Pr(NO3)2 E4]3[Pr(NO3)6]. Fig 7 Assumed transition state model in asymmetric aldol reaction using Pr3+-1.
7 Table 3 Asymmetric aldol reactions using Pr(OTf)3 and 1 Scheme 4 Reversal of the sense of enantioselection. Vol.61 No ( 49 ) 451
8 Table 4 Asymmetric aldol reactions using Pr(OTf)3 and 1 C.-H. Wong, Angew. Chem., Int. Ed., 39, 1352 (2000); (b) E. M. Carreira, "Comprehensive Asymmetric Catalysis" eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg, 1999, Vol. 3, p 998; (c) R. Mahrwald, Chem. Rev., 99, 1095 (1999); (d) H. Groger, E. M. Vogl, M. Shibasaki, Chem. Eur. J., 4, 1137 (1998); (e) S. G. Nelson, Tetrahedron: Asymmery, 9, 357 (1998) 2) T. Mukaiyama, K. Narasaka, K. Banno, Chem. Lett., 1973, ) (a) "Organic Synthesis in Water" ed. by P. A. Grieco, Blackie Academic and Professional, London, 1998; (b) C.-J. Li, T.-H. Chan, "Organic Reactions in Aqueous Media" John Wiley & Sons, New York, ) (a) S. Kobayashi, Chem. Lett., 1991, 2187; (b) S. Kobayashi, I. Hachiya, J. Org. Chem., 59, 3590 (1994) 5) (a) S. Kobayashi, Synlett, 1994, 689; (b) S. Kobayashi, "Lanthanides: Chemistry and Use in Organic Synthesis" ed. by S. Kobayashi, Springer, Berlin, 1999, p 63; (c) S. Kobayashi, Eur. J. Org. Chem., 1999, 15; (d) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev., 102, 2227 (2002) 6) (a) D. Sinou, Adv. Synth. Catal., 344, 221 (2002); (b) U. M. Lindstrom, Chem. Rev., 102, 2751 (2002); (c) K. Manabe, S. Kobayashi, Chem. Eur. J., 8, 4094 (2002) Nagayama, T. Busujima, Chem. Lett., 1999, 71; (b) idem, Tetrahedron, 55, 8739 (1999); (c) S. Kobayashi, Y. Mori, S. Nagayama, K. Manabe, Green Chem., 1, 175 (1999); (d) S. Nagayama, S. Kobayashi, J. Am. Chem. Soc., 122, (2000) 8) S. Kobayashi, T. Hamada, S. Nagayama, K. Manabe, Org. Lett., 3, 165 (2001) 9) T. Hamada, K. Manabe, S. Ishikawa, S. Nagayama, M. Shiro, S. Kobayashi, J. Am. Chem. Soc., 125, 2989 (2003) 10) F. A. Hart, "Comprehensive Coordination Chemistry" eds. by G. Wilkinson, R. D. Gillard, J. A. McCleverty, Pergamon Press, Oxford, 1987, Vol. 3, Chapter 39 Sharpless, Angew. Chem., Int. Ed., 34, 1059 (1995); (b) S. E. Denmark, T. Wynn, J. Am. Chem. Soc., 123, 6199 (2001)
9 16) (a) E. P. Kyba, M. G. Siegel, L. R. Sousa, G. D. Y. Sogah, D. J. Cram, J. Am. Chem. Soc., 95, 2691 (1973); (b) E. P. Kyba, G. W. Gokel, F. de Jong, K. Koga, L. R. Sousa, M. G. Siegel, L. Kaplan, G. D. Y. Sogah, D. J. Cram, J. Org. Chem., 42, 4173 (1977) 17) J. S. Bradshaw, P. Huszthy, C. W. McDaniel, C. Y. Zhu, N. K. Dalley, R. M. Izatt, S. Lifson, J. Org. Chem., 55, 3129 (1990) Vol.61 No ( 51 ) 453
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