Novel Concept for Efficient Transition-Metal-Catalyzed Reactions: A Highly Diastereoselective Titanocene-Catalyzed Pinacol Coupling under Buffered Protic Conditions

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2070-2071

  Gansäuer, Andreas ^a   Bauer, Daniel ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039750771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9801418     Document Type: Article

References (18)

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10. For stoichiometric pinacol couplings initiated by low-valent titanium reagents, see: (a) Raubenheimer, H. G.; Seebach, D. Chimia 1986, 40, 12. (b) Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 28, 5717. (c) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
11. For stoichiometric pinacol couplings initiated by low-valent titanium reagents, see: (a) Raubenheimer, H. G.; Seebach, D. Chimia 1986, 40, 12. (b) Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 28, 5717. (c) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
12. For stoichiometric pinacol couplings initiated by low-valent titanium reagents, see: (a) Raubenheimer, H. G.; Seebach, D. Chimia 1986, 40, 12. (b) Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 28, 5717. (c) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
13. Handbook of Chemistry and Physics, 78th ed.; CRC Press: Boca Raton, FL, 1997; pp 8-45-8-55.
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15. (b) Gansäuer, A.; Bauer, D. Unpublished results.
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17. (b) Stephan, D. W. Organometallics 1992, 11, 996.
18. 4) and evaporation of the solvent, the crude product was purified by flash chromatography (petroleum ether, t-BuOMe, 1:1) to give 373 mg of (4,4′-dimethoxydiphenyl)-1,2-ethanediol as a 99:1 mixture of 1:2 (91%).