Abstract
The review describes the mechanism of chiral discrimination of racemic amines upon crystallization and the induction of chirality in organic reactions by using them as chiral auxiliaries. In order to form conglomerates, which can be resolved into the two enantiomers upon alternative seeding, both formation and packing of 21-columns are essentially very important. On the other hand, in order to achieve high efficiency in resolution through diastereomeric salt formation, which is the most practical method, one of a pair of diastereomeric salts derived from a racemic amine and an enantiomerically pure resolving agent should at least have two 21-columns and planar boundary surfaces in its crystal structure. On the basis of this knowledge, we developed several artificial chiral auxiliaries such as erythro-2-amino-1,2-diphenylethanol,cis-2-amino-1-acenaphthenol, andcis-2-amino-3,3-dimethyl-1-indanol. These were found to be very efficient chiral auxiliaries in asymmetric inductions: alkylation of chiral imines, catalytic borane-reduction, and alkylation of chiral N-acylated oxazolidinone.
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References
Abiko A, Moriya O, Filla S A and Masamune S 1995Angew. Chem., Int. Ed. Engl. 34 793
Bartczak A W, Sangaiah R, Kelman D J, Toney G E, Deterding L J, Charles J, Marbury G D and Gold A 1989Tetrahedron Lett. 30 1109
Brianso P M-C, Leclercq M and Jacques J 1979Acta Crystallogr. B35 2751
de Diego H L 1994Acta Chem. Scand. 48 306
Evans D A, Ennis M D and Mathre D J 1982J. Am. Chem. Soc. 104 1737
Fuji K, Kawabata T, Kuroda A and Taga T 1995J. Org. Chem. 60 1914
Hashimoto K, Sumida Y, Terada S and Okamura K 1993J. Mass Spectrom. Soc. Jpn. 41 87
Hashimoto Y, Takaoki K, Sudo A, Ogasawara T and Saigo K 1995Chem. Lett. 235
Hayashi T, Ohno A, Lu S, Matsumoto Y, Fukuyo E and Yanagi K 1994J. Am. Chem. Soc. 116 4221
Hoover J R E, Dunn G L, Jakas D R, Lam L L, Taggart J J, Guarini J R and Phillips L 1974J. Med. Chem. 17 34
Ishihara K and Yamamoto H 1994J. Am. Chem. Soc. 116 1561
Jacques J, Collet A and Wilen S H 1981aEnantiomers, racemates and resolutions (New York: John Wiley and Sons)
Jacques J, Leclercq M and Brienne M-J 1981bTetrahedron 37 1727
Kinbara K, Hashimoto Y, Sukegawa M, Nohira H and Saigo K 1996aJ. Am. Chem. Soc. 118 3441
Kinbara K, Sakai K, Hashimoto Y, Nohira H and Saigo K 1996bTetrahedron: Asym. 7 1539
Kinbara K, Sakai K, Hashimoto Y, Nohira H and Saigo K 1996cJ. Chem. Soc., Perkin Trans. 2 (in press)
Kuroki T, Hamada T and Katsuki T 1995Chem. Lett. 339
Maruoka K, Saito S and Yamamoto H 1995J. Am. Chem. Soc. 117 1165
Newman P 1981Optical resolution procedures for chemical compounds (New York: Optical Resolution Information Center) vol. 1
Saigo K, Ogawa S, Kikuchi S, Kasahara A and Nohira H 1982Bull. Chem. Soc. Jpn. 55 1568
Sudo A and Saigo K 1995Tetrahedron: Asym. 6 2153
Sudo A, Hashimoto Y, Kimoto H, Hayashi K and Saigo K 1994Tetrahedron: Asym. 5 1333
Sudo A, Matsumoto M, Hashimoto Y and Saigo K 1995Tetrahedron: Asym. 6 1853
Weijland J, Pfister K, 3rd, Swanezy E F, Robinson C A and Tishler M 1951J. Am. Chem. Soc. 73 1216
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Saigo, K., Hashimoto, Y., Kinbara, K. et al. Molecular-level chiral discrimination and induction. Formerly: Proceedings (Chemical Sciences) 108, 555–573 (1996). https://doi.org/10.1007/BF02896330
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DOI: https://doi.org/10.1007/BF02896330