Highly efficient, catalytic Meerwein-Ponndorf-Verley reduction with a novel bidentate aluminum catalyst

Angewandte Chemie - International Edition

Volumn 37, Issue 17, 1998, Pages 2347-2349

  Ooi, Takashi ^a   Miura, Tomoya ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aluminum; Asymmetric synthesis; Homogeneous catalysis; Oxidations; Reductions

Indexed keywords

EID: 0032544562     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980918)37:17<2347::AID-ANIE2347>3.0.CO;2-U     Document Type: Article

References (27)

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19. 3 (1 equiv) in 2-propanol did not proceed at room temperature.
20. 2 at room temperature for 1 h gave rise to 4-phenylcyclohexanone in only 8% yield.
21. J. D. Morrison, H. S. Mosher, Asymmetric Organic Reactions, American Chemical Society, Washington, DC, 1976, p. 160. Evans et al. reported the first catalytic and highly enantioselective MPV reduction with a chiral Sm complex: D. A. Evans, S. G. Nelson, M. R. Gagne, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800.
22. J. D. Morrison, H. S. Mosher, Asymmetric Organic Reactions, American Chemical Society, Washington, DC, 1976, p. 160. Evans et al. reported the first catalytic and highly enantioselective MPV reduction with a chiral Sm complex: D. A. Evans, S. G. Nelson, M. R. Gagne, A. R. Muci, J. Am. Chem. Soc. 1993, 115, 9800.
23. The enantiomeric excess of 7 was determined by comparison of the optical rotation with that of commercially available 7 (98% ee). In the reaction with (R)-(+)-sec-obromophenethyl alcohol the ee value was measured after conversion into the corresponding styrene oxide: H. C. Kolb, K. B. Sharpless, Tetrahedron 1992, 48, 10515.
24. Unfortunately, the asymmetric MPV reduction of dialkyl ketones gave unsatisfactory results in terms of reactivity and selectivity. For example, reaction of 2-undecanone under similar conditions with (R)-(+)-sec-o-bromophenethyl alcohol afforded 2-undecanol in 11% yield with less than 25% ee.
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