Reaction of α,β-unsaturated ketones with LiAlH4 under oxygen: Synthesis of 1,3-diols

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6485-6487

  Csákÿ, Aurelio G ^a   Máximo, Natalia ^a   Plumet, Joaquín ^a   Rámila, Ainhoa ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Diols; Ketones; Oxygenation; Reduction

Indexed keywords

KETONE;

ARTICLE; CHEMICAL REACTION; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033609868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01270-8     Document Type: Article

References (11)

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3. See for instance: (a) Oishi, T.; Nakata, T. Synthesis 1990, 635-645.
4. (b) Enders, D.; Hundertmark, T.; Lampe, C.; Jegelka, U.; Scharfbillig, I. Eur. J. Chem. 1998, 2839-2849 and references cited therein.
5. 2O (30 mL) containing NaOH (3 mmol). The solution was stirred from 0°C to it for 24 h. Compounds 1b-e precipitated out of the solution upon addition of water (20 mL) and cooling the mixture at 0°C. This procedure can be easily scaled to the multi-gram synthesis of these starting materials.
6. 2O.
7. For the hydroalumination of C=C bonds, see: Eisch, J. J In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 8, Chapter 3.11. See also:
8. (a) Snyder, E. I. J. Org. Chem. 1967, 32, 3531-3534.
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10. For a deracemization procedure of 1,3-diols, see: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346-12347.
11. For the spontaneous resolution of racemic 1,3-diphenylpropane-1,3-diol, see: Dale, J. Chem. Soc. 1961, 910-922.