Water-Accelerated Tandem Claisen Rearrangement-Catalytic Asymmetric Carboalumination

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1503-1505

  Wipf, Peter ^a   Ribe, Seth ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

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EID: 0001226423     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015816z     Document Type: Article

References (15)

1. Wipf, P.; Ribe, S. Org. Lett. 2000, 2, 1713.
2. (a) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
3. (b) Kondakov, D. Y.; Negishi, E.-I. J. Am. Chem. Soc. 1996, 118, 1577.
4. Ribe, S.; Kondru, R. K.; Beratan, B. N.; Wipf, P. J. Am. Chem. Soc. 2000, 122, 4608.
5. Wipf, P.; Lim, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1068.
6. For a review, see: Wipf, P.; Ribe, S. Chem. Commun. 2001, 299.
7. Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D., Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590.
8. The enantiomeric excess was determined by conversion to the corresponding bis-Mosher ester derivatives. The absolute configuration was assigned in analogy to refs 1-3.
9. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., I. Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 827-874.
10. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
11. (a) Lutz, R. P. Chem. Rev. 1984, 84, 205.
12. (b) Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
13. (c) Sharma, G. V. M.; Ilangovan, A.; Sreenivas, P.; Mahalingam, A. K. Synlett 2000, 615.
14. 2 demonstrated the highest acceleration in this rearrangement, but only reduced alkane was isolated. See also: Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095.
15. Yang, X. M.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.