Asymmetric reduction of aromatic ketones: Importance of the conformation of the aromatic group

Tetrahedron Asymmetry

Volumn 9, Issue 19, 1998, Pages 3365-3369

  Manju, Kavita ^a   Trehan, Sanjay ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; KETONE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHROMATOGRAPHY; CONFORMATIONAL TRANSITION; ENANTIOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TEMPERATURE;

EID: 0032476140     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00347-4     Document Type: Article

References (16)

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3. (c) Midland, M. M. Chem. Rev. 1989, 89, 1553.
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9. Nevalainen, V. Tetrahedron: Asymmetry 1991, 429.
10. Molecular mechanics calculations (MMX force field incorporated into the PC MODEL Program) were carried out using Serena Software, Bloomington, IN.
11. MM2 force field gives reasonable rotational barriers for aromatic systems, for an example see: Broeker, J. L.; Hoffman, R. W.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5006.
12. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
13. In an extreme example, the phenyl group preferentially occupies an axial position as compared to the methyl group in cyclohexane, see; Eliel, E. L.; Manoharan, M. J. Org. Chem. 1981, 46, 1959.
14. Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 611.
15. Slightly lower enantioselectivity was obtained when borane and ketones were added simultaneously.
16. Trost, B. M.; Bunt, R. C.; Pulley, S. R. J. Org. Chem. 1994, 59, 4202.