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Products > TCI Topics Archives > TCI Topics 2014 >

Useful Cinchona Alkaloid Derived Catalysts

A cinchona alkaloid derivative, β-isocupreidine (β-ICD, 1), has been known as a catalyst which catalyzes reactions such as the Morita–Baylis–Hillman (MBH) reaction¹⁾, aza-MBH reaction²⁾, Michael reaction³⁾, electrophilic amination⁴⁾, and [2+2] cycloaddition^5,6) with high enantioselectivities. Recently, Hatakeyama, Ishihara, et al. have developed α-isocupreine (α-ICPN, 2), a pseudoenantiomer of 1, and reported the MBH reaction using 2.⁷⁾ According to their results, in the reaction of various aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA), the catalyst 1 affords (R)-products, and the catalyst 2 affords the related (S)-isomers respectively, in good yields. Thus, both enantiomers can be obtained in various kinds of asymmetric reactions by using these two catalysts properly. This synthetic method has broad applicability to the synthesis of natural products.

References

1) β-Isocupreidine-catalyzed asymmetric Baylis–Hillman reactions
- a) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
- b) A. Nakano, S. Kawahara, S. Akamatsu, K. Morokuma, M. Nakatani, Y. Iwabuchi, K. Takahashi, J. Ishihara, S. Hatakeyama, Tetrahedron 2006, 62, 381.
2) β-Isocupreidine-catalyzed asymmetric Baylis−Hillman reaction of imines
- a) S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103.
- b) M. Shi, Y.-M. Xu, Angew. Chem. Int. Ed. 2002, 41, 4507.
3) Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition
- H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. Int. Ed. 2005, 44, 105.
4) Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of α-substituted α-cyanoacetates and β-dicarbonyl compounds
- S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120.
5) Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions: Catalytic, asymmetric synthesis of bicyclic β-lactones
- G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945.
6) Organocatalyzed formal [2 + 2] cycloaddition of ketimines with allenoates: Facile access to azetidines with a chiral tetrasubstituted carbon stereogenic center
- S. Takizawa, F. A. Arteaga, Y. Yoshida, M. Suzuki, H. Sasai, Org. Lett. 2013, 15, 4142.
7) α-Isocupreine, an enantiocomplementary catalyst of β-isocupreidine
- a) Y. Nakamoto, F. Urabe, K. Takahashi, J. Ishihara, S. Hatakeyama, Chem. Eur. J. 2013, 19, 12653.
- b) S. Hatakeyama, J. Ishihara, K. Takahashi, Y. Nakamoto, Nagasaki University, Jpn. Kokai Tokkyo Koho 2013 227272, 2013.

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