Asymmetric induction by β-cyclodextrins in NaBH4 reduction of ketones

Journal of Inclusion Phenomena and Molecular Recognition in Chemistry

Volumn 27, Issue 1, 1997, Pages 41-48

  Park, Kwanghee Koh ^a   Sim, Woo Jeon ^a   Park, Joon Woo ^b  

^a Chungnam National University   (South Korea)

^b Ewha Womans University   (South Korea)

Author keywords

Asymmetric induction; Enantioselectivity; Reduction; Sodium borohydride; cyclodextrin

Indexed keywords

EID: 0030642474     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1007937115071     Document Type: Article

References (25)

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3. (c) references cited in Refs. 2-8.
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17. (d) ibid., Vol. 4, p. 4172.
18. (e) ibid., Vol. 4, p. 4173.
19. (f) ibid., Vol. 5, p. 5217.
20. (g) ibid., Vol. 3, p. 3297.
21. -1. The association constants of other substrates would be greater than this value as they have greater hydrophobicity and fit better into the β-CD cavity [1].
22. 14. T.S. Straub and M.L. Bender: J. Am. Chem. Soc. 94, 8881 (1972).
23. 15. H.J. Brass and M.L. Bender: J. Am. Chem. Soc. 95, 5391 (1973).
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25. 17. Dissociation of hydroxyl groups is supported by a large increase in solubility of β-CD in the reaction condition; solubility of β-CD in water is 1.85 g/100 ml [1], which gives 16.2 mM for saturated solution.