Stereocontrol in Homogeneous Catalytic Hydrogenation via Hydroxyl Group Coordination

Journal of the American Chemical Society

Volumn 105, Issue 4, 1983, Pages 1072-1073

  Stork, Gilbert ^a   Kahne, Daniel E ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845551063     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00342a080     Document Type: Article

References (15)

1. Inter alia: Eisenbraun, E.J.; George, T.; Riniker, B.; Djerassi, C. J. Am. Chem. Soc. 1960, 82, 3648.
2. Thompson, H.W.; Naipawer, R.E. J. Am. Chem. Soc. 1973, 95, 6379.
3. Thompson, H.W.; McPherson, E. J. Am. Chem. Soc. 1974, 96, 6232.
4. Fujimoto, R.; Kishi, Y.; Blount, J. J. Am. Chem. Soc. 1980, 102, 7154.
5. For some interesting examples of moderate asymmetric induction in acyclic unsaturated alcohols, using a rhodium catalyst, see, however: Brown, J.M.; Naik, R.G.J. Chem. Soc, Chem. Commun. 1982, 348.
6. Crabtree, R.H.; Felkin, H.; Fellebeen-Khan, T.; Morris, G.E. J. Organomeu Chem. 1979, 168, 183.
7. Suggs, J.W.; Cox, S.D.; Crabtree, R.H.; Quirk, J.M. Tetrahedron Lett. 1981, 303. After completion of the work in this paper, we learned that Crabtree et al. have begun to look at directing effects in hydrogenation with the iridium catalyst and that they have observed such an effect in the case of terpinen-4-ol.
8. Boyce, C.B.C.; Whitehurst, J.S. J. Chem. Soc. 1960, 4547.
9. Hajos, Z.G.; Parrish, D.R. J. Org. Chem. 1973, 38, 3239.
10. Baggaley, K.H.; Brooks, S.G.; Green, J.; Redman, B.T. J. Chem. Soc. C 1971, 2671.
11. Stork, G.; Shiner, C.; Winkler, J.J. Am. Chem. Soc. 1982, 104, 310.
12. The stereochemistry of these compounds was assigned by comparison (NMR, GC) with authentic compounds made from the Diels-Alder adducts of methyl acrylate and 1, 3-pentadiene (prepared in this laboratory by Dr. K. Atwal; cf.: Nakagawa, K.; Sawai, M.; Iishi, Y.; Ogawa, M. Bull. Chem. Soc. Jpn. 1977, 50, 2487), followed by Pd-charcoal hydrogenation and lithium aluminum hydride reduction.
13. Correlated by comparison (mp, NMR, IR) of the carboxylic acids obtained by Jones oxidation of the alcohol mixture from the hydrogenations with authentic materials: Wolff, S.; Agosta, W.C. J. Am. Chem. Soc. 1973, 38, 1694.
14. The stereochemistry was established by comparison (NMR, GC) with authentic substances made by hydride reduction of the related ketones: Brown, H.C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159. Dauben, W.G.; Fonken, G.J.; Noyce, D.S.J. Am. Chem. Soc. 1956, 78, 2579.
15. The stereochemistry was established by use of the 1Hand 13C NMR data reported in the following: Grenier-Coustalot, M.F.; Zahidi, A.; Bonastre, J.; Grenier, P. Bull. Soc. Chim. Fr. 1979, 229. Rei, M.-H.J. Org. Chem. 1979, 44, 2760.