Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols

Organic Letters

Volumn 1, Issue 3, 1999, Pages 367-369

  Jung, Michael E ^a   Pontillo, Joseph ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; KETONE; RHODIUM;

ARTICLE; CATALYSIS; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; CATALYSIS; KETONES; MOLECULAR CONFORMATION; RHODIUM; STEREOISOMERISM;

EID: 0033549674     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9900257     Document Type: Article

References (14)

1. Recipient of UCLA Distinguished Teaching Assistant Award.
2. (a) Sharma, P.; Alam, M. J. Chem. Soc., Perkin Trans. 1 1988, 2537.
3. (b) Alam, M.; Sharma, P.; Zektzer, A. S.; Martin, G. E.; Ji, X.; Van der Helm, D. J. Org. Chem. 1989, 54, 1896.
4. Cooke, M. P., Jr. J. Org. Chem. 1979, 44, 2461.
5. a) Paulissen, R.; Reimlinger, H.; Hayez, E.; Hubert, A. J.; Teyssié, P. Tetrahedron Lett. 1973, 24, 2233.
6. (b) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
7. (c) This reaction has been reported on propargylic alcohols using diazoacetates: Noels, A. F.; Demonceau, A.; Petiniot, N.; Hubert, A. J.; Teyssié, P. Tetrahedron 1982, 38, 2733.
8. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
9. (a) Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913.
10. (b) Marshall, J. A.; Robinson, E. D.; Zapata, A. J. Org. Chem. 1989, 54, 5854.
11. Doyle, M. P.; Bagheri, V.; Claxton, E. E. J. Chem. Soc., Chem. Commun. 1990, 46.
12. For a different rearrangement of a secondary allylic alcohol with methyl diazoacetoacetate, see: Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1995, 117, 10413. In this case, an intermediate very similar to V undergoes a [3,3] sigmatropic shift rather than the [2,3] shift we observe here.
13. Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748.
14. See following Letter (Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371). We thank Professor Wood for communication of these results prior to publication.