Chiral boron enolate aldol additions to chiral aldehydes

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4629-4632

  Dias, Luiz C ^a   Aguilar, Andrea M ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750057699     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0618712     Document Type: Article

References (52)

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40. (c) We use the "Felkin" descriptor to refer to the diastereomer predicted by the Felkin-Ahn paradigm. The "anti-Felkin" descriptor refers to diastereomers not predicted by this transition state model.
41. 13C NMR spectroscopic analysis of the unpurified product mixture;
42. (b) All of the percentage values represent data obtained from at least three individual trials.
43. Roush, W. R.; Bannister, T. D.; Wendt, M. D.; VanNieuwenhze, M. S.; Gustin, D. J.; Dilley, G. J.; Lane, G. C.; Scheidt, K. A.; Smith, W. J., III. J. Org. Chem. 2002, 67, 4284.
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46. Dias, L. C.; Aguilar, A. M.; Salles, A. G., Jr.; Steil, L. J.; Roush, W. R. J. Org. Chem. 2005, 70, 10461.
47. Having confirmed the relative relationship between boron enolate-derived stereogenic centers, the absolute stereochemistry of the newly formed hydroxyl substituent was determined by ascertaining its relationship to the known stereocenter originating from the aldehydes.
48. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 889.
49. Several computational studies indicate that chairlike and boatlike transiton states in methyl ketone aldol reactions are relatively close in energy: (a) Li, Y.; Paddow-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 1535.
50. (b) Bernardi, F.; Robb, M. A.; Suzzi-Vall, G.; Tagliavini, E.; Trombin, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 6472.
51. For papers dealing with the origins of remote asymmetric induction in these reactions, see: (a) Paton, R. S.; Goodman, J. M. Org. Lett. 2006, 8, 4299-4302.
52. (b) Stocker, B. L.; Teesdale-Spittle, P.; Hoberg, J. O. Eur. J. Org. Chem. 2004, 330.