Efficient acyclic stereocontrol using the tethered aminohydroxylation reaction

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2583-2585

  Donohoe, Timothy J ^a   Johnson, Peter D ^a   Pye, Richard J ^a   Keenan, Martine ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; OXIDATION; STEREOCHEMISTRY; STEREOSPECIFICITY; TETHERED AMINOHYDROXYLATION REACTION;

EID: 4043171449     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049136i     Document Type: Article

References (20)

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13. Ratios of > 10:1 mean that we could not detect the other diastereoisomer in the NMR spectra of the products.
14. The stereochemistry of 2 was deduced by hydrolysis of the oxazolidinone ring and conversion of the stereoisomers to their respective triacetates which were separable. Symmetry properties then allowed assignment of the syn and anti products.
15. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. See also: Adam, W.; Mitchell, C. M.; Sana-Möller, C. R. J. Org. Chem. 1999, 64, 3699. Donohoe, T. J.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1999, 40, 6881. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.
16. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. See also: Adam, W.; Mitchell, C. M.; Sana-Möller, C. R. J. Org. Chem. 1999, 64, 3699. Donohoe, T. J.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1999, 40, 6881. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.
17. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. See also: Adam, W.; Mitchell, C. M.; Sana-Möller, C. R. J. Org. Chem. 1999, 64, 3699. Donohoe, T. J.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1999, 40, 6881. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.
18. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. See also: Adam, W.; Mitchell, C. M.; Sana-Möller, C. R. J. Org. Chem. 1999, 64, 3699. Donohoe, T. J.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1999, 40, 6881. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.
19. The stereochemistry of TA product 18 was deduced by base cleavage of the oxazolidinone ring and conversion of the stereoisomers to their respective triacetates. Hydrogenation of the double bond formed a common intermediate from previous studies. 7
20. Thomas, S.; Lim, P. J.; Gable, R. W.; Young, C. G. Inorg. Chem. 1998, 37, 590.