Scope of the nickel catalyzed asymmetric reductive ring opening reaction. Synthesis of enantiomerically enriched cyclohexenols

Tetrahedron

Volumn 54, Issue 7, 1998, Pages 1107-1116

  Lautens, Mark ^a   Rovis, Tomislav ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; NICKEL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032510180     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10211-3     Document Type: Article

References (25)

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12. b) For the use of functionalized cyclohexanes in organic synthesis and approaches to prepare them, see: Ferrier, R.J.; Middleton, S. Chem. Rev., 1993, 93, 2779. Oh, T.; Reilly, M. Org. Prep. Proceed. Int. 1994, 26, 129. Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
13. b) For the use of functionalized cyclohexanes in organic synthesis and approaches to prepare them, see: Ferrier, R.J.; Middleton, S. Chem. Rev., 1993, 93, 2779. Oh, T.; Reilly, M. Org. Prep. Proceed. Int. 1994, 26, 129. Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
14. b) For the use of functionalized cyclohexanes in organic synthesis and approaches to prepare them, see: Ferrier, R.J.; Middleton, S. Chem. Rev., 1993, 93, 2779. Oh, T.; Reilly, M. Org. Prep. Proceed. Int. 1994, 26, 129. Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
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17. 8. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Also see Fraenkel, G.; Dix., D. T.; Carlson, M. Tetrahedron Lett. 1968, 5, 579 and Eisch, J. J. Comprehensive Organic Synthesis; B.M. Trost, Ed.; Pergamon Press: Oxford, 1991; Vol. 8. pg. 733.
18. 8. Eisch, J. J.; Fichter, K. C. J. Organomet. Chem. 1983, 250, 63. Also see Fraenkel, G.; Dix., D. T.; Carlson, M. Tetrahedron Lett. 1968, 5, 579 and Eisch, J. J. Comprehensive Organic Synthesis; B.M. Trost, Ed.; Pergamon Press: Oxford, 1991; Vol. 8. pg. 733.
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21. 13C NMR spectrum.
22. 2 see: Schunn, R. A.; Ittel, S. D.; Cushing, M. A. Inorg. Synth. 1990, 28, 94.
23. 12. Lautens, M.; Rovis, T. to appear in J. Org. Chem.
24. Compound 17 has also been prepared by an alternate route prior to our work: see (a) Boyd, D. R.; McMordie, R. A. S.; Sharma, N. D.; Dalton, H.; Williams, P.; Jenkins, R. O. J. Chem. Soc., Chem. Commun. 1989, 339.
25. (b) Boyd, D. R.; Sharma, N. D.; Kerley, N.A.; McMordie, R. A. S.; Sheldrake, G.N.; Williams, P.; Dalton, H.; J. Chem. Soc., Perkin Trans. I, 1996, 67.