Catalytic asymmetric synthesis of α-alkylidene-β-hydroxy esters via dynamic kinetic asymmetric transformation involving Ba-catalyzed direct aldol reaction

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 10842-10843

  Yamaguchi, Akitake ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; ALKENYL; ALKYLIDENES; ASYMMETRIC SYNTHESIS; CHEMICAL EQUATIONS; DIRECT ALDOL REACTION; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS; HYDROXY ESTERS; UNSATURATED ESTERS;

ALDEHYDES; BARIUM; ESTERIFICATION; PROTON TRANSFER;

ESTERS;

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALDEHYDE; ALKENYL GROUP; BARIUM; ESTER DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROTON;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; DONOR; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATION; ISOMERIZATION;

ALDEHYDES; BARIUM; CATALYSIS; ESTERS; ISOMERISM; KINETICS;

EID: 68249139771     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904575e     Document Type: Article

References (31)

1. For a general review of asymmetric aldol reactions, see: Geary, L. M.; Hultin, P. G. Tetrahedron: Asymmetry 2009, 20, 131.
2. Reviews of direct aldol reactions: (a) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
3. For organocatalytic directaldol reactions, also see: (b) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
4. (c) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
5. (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
6. (b) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71.
7. (a) Trost, B. M.; Malhotra, S.; Fried, B. A. J. Am. Chem. Soc. 2009, 131, 1674.
8. For early works, also see: (b) Yao, W.; Wang, J. Org. Lett. 2003, 5, 1527.
9. (c) Hasegawa, K.; Arai, S.; Nishida, A. Tetrahedron 2006, 62, 1390.
10. (a) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685.
11. For early works, also see: (b) Gasparski, C. M.; Miller, M. J. Tetrahedron 1991, 47, 5367.
12. (c) Yoshikawa, N.; Shibasaki, M. Tetrahedron 2002, 58, 8289.
13. Thiazolidinethione: (a) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
14. Malonic acid half thioester: (b) Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284.
15. (c) Fortner, K. C.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 1032. α-Isothiocyanato imide:
16. d) Willis, M. C.; Cutting, G. A.; Piccio, V. J.-D.; Durbin, M. J.; John, M. P. Angew. Chem., Int. Ed. 2005, 44, 1543.
17. (e) Li, L.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 12248.
18. Alkylnitrile: (f) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757.
19. For alternative catalytic asymmetric C-C bond-forming reactions for chiral β-hydroxy ester synthesis, see the following reviews: (a) Catalytic asymmetric reductive aldol reactions: Garner, S. A.; Krische, M. J. In Modern Reduction Methods; Andersson, P. G., Munslow, I. J., Eds.; Wiley-VCH: Weinheim, Germany, 2008; p 387.
20. (b) Catalytic asymmetric Morita-Baylis-Hillman reactions: Masson, G.; Housseman, C.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 4614.
21. For a review of DYKAT, see: (a) Steinreiber, J.; Faber, K.; Griengl, H. Chem.-Eur. J. 2008, 14, 8060.
22. For DYKAT involving a aldol/retro-aldol sequence, see: (b) Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601.
23. (c) Gnanadesikan, V.; Horiuchi, Y.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7782.
24. (d) Córdova, A.; Ibrahem, I.; Casas, J.; Sundén, H.; Engqvist, M.; Reyes, E. Chem.-Eur. J. 2005, 11, 4772.
25. (e) Steinreiber, J.; Schürmann, M.; Wolberg, M.; van Assema, F.; Reisinger, C.; Fesko, K.; Mink, D.; Griengl, H. Angew. Chem., Int. Ed. 2007, 46, 1624.
26. For a review of alkaline-earth metal catalysts for direct C-C bond-forming reactions, see: (a) Kazmaier, U. Angew. Chem., Int. Ed. 2009, 48, available online (DOI: 10.1002/anie.200901261).
27. For examples of chiral Ba aryloxide catalysts, see: (b) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
28. (c) Saito, S.; Kobayashi, S. J. Am. Chem. Soc. 2006, 128, 8704.
29. (d) Yamatsugu, K.; Yin, L.; Kamijo, S.; Kimura, Y.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2009, 48, 1070.
30. β,γ-Unsaturated esters have been used for direct catalytic asymmetric Mannich-type reactions (see: Yamaguchi, A.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2007, 9, 3387.). Benzyl crotonate (α,β-unsaturated ester) was not applicable for the present system because the γ-proton in crotonate is less acidic than the α-proton in β,γ-unsaturated esters.
31. Detailed results comparing (S)-Ba-1a with (S)-Ba-1b are shown in the Supporting Information.