Diastereoselective Rh-mediated construction of 2,3,5-trisubstituted tetrahydrofurans

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6706-6712

  Taber, Douglass F ^a   Song, Ying ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029798205     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960758u     Document Type: Article

References (45)

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11. For leading references to Rh-mediated intramolecular C-H insertions see: (a) Taber, D. F. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; p 1127. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (c) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (d) Doyle, M. P.; Dyatkin. A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (e) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 16, 3296. (f) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis: Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (g) Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 1045.
12. For leading references to Rh-mediated intramolecular C-H insertions see: (a) Taber, D. F. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; p 1127. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (c) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (d) Doyle, M. P.; Dyatkin. A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (e) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 16, 3296. (f) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis: Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (g) Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 1045.
13. For leading references to Rh-mediated intramolecular C-H insertions see: (a) Taber, D. F. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; p 1127. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (c) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (d) Doyle, M. P.; Dyatkin. A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (e) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 16, 3296. (f) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis: Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (g) Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 1045.
14. For leading references to Rh-mediated intramolecular C-H insertions see: (a) Taber, D. F. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; p 1127. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (c) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (d) Doyle, M. P.; Dyatkin. A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (e) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 16, 3296. (f) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis: Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (g) Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 1045.
15. For leading references to Rh-mediated intramolecular C-H insertions see: (a) Taber, D. F. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; p 1127. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (c) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (d) Doyle, M. P.; Dyatkin. A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (e) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 16, 3296. (f) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis: Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (g) Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 1045.
16. For leading references to Rh-mediated intramolecular C-H insertions see: (a) Taber, D. F. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; p 1127. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (c) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (d) Doyle, M. P.; Dyatkin. A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (e) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 16, 3296. (f) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis: Moser, W. R., Slocum, D. W., Eds.; ACS Advanced Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (g) Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 1045.
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18. (b) For a detailed account of regioselectivity and diastereoselectivity in the Rh-mediated cyclization of α-diazo-β-keto esters, see: Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686.
19. (a) For the first report of the highly diastereocontrolled cyclization of a substituted α-diazo ester, see: Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757.
20. (b) For a computational model that rationalizes the diastereoselectivity of intramolecular Rh-mediated C-H insertion, see: Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547.
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