Biaryl hydroxy aldehydes as intermediates in the metal-assisted atropo- enantioselective reduction of biaryl lactones: Structures and aldehyde- lactol equilibria

Tetrahedron

Volumn 54, Issue 36, 1998, Pages 10677-10690

  Bringmann, Gerhard ^a   Breuning, Matthias ^a   Endress, Heike ^a   Vitt, Daniel ^a   Peters, Karl ^b   Peters, Eva Maria ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HYDROXYALDEHYDE; LACTONE; METAL; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032480394     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00618-8     Document Type: Article

References (33)

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2. 2. (a) Bringmann, G.; Walter, R.; Weírich, R. Angew. Chem. 1990, 102, 1006-1019; Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991.
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26. 17. A similar formation of a bisacetal under mild conditions was reported for the related system isochroman-1-ol /2-(2-hydroxyethyl)benzaldehyde: Rieche, A.; Schmitz, E. Chem. Ber. 1956, 89, 1254-1262.
27. 18. For a review on acetals see: Meskens, F. A. J. Synthesis 1981, 501-522.
28. 19. For the equilibrium between open-chain hydroxy ketones and cyclic semiacetals in various solvents, see: Whiting, J. E.; Edward, J. T. Can. J. Chem. 1971, 3799-3806.
29. 20. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon Press: New York, 1983; pp. 5-49.
30. 21. Lemieux, R. U.; Pavia, A. A.; Martin, J. C.; Watanabe, K. A. Can. J. Chem. 1969, 47, 4427-4439.
31. f (ax-7d - eq-7d) = -0.77 kcal/mol.
32. 3.
33. 24. Bringmann, G.; Breuning, M. Synlett, in preparation.