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Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 183-186

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doi:10.1016/S0040-4039(00)83972-6

Efficient asymmetric hydrogenations of camphor-soltam-imide-conjugated alkenes.

Wolfgang Oppolzer, Robert J. Mills and Marius Reglier

Département de Chimie Organique, Université de Gen e, CH-1211 Genève, Switzerland

Received 25 October 1985.

Available online 8 March 2001.

Abstract

The trisubstituted olefinic bond of sultam-imides was hydrogenated in the presence of Pd/C with>90% diastereoface discrimination to give after saponification recovered auxiliary and the β-substituted carboxylic acids or in high e.e..

References

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W.S. Knowles, M.J. Sabacky, B.D. Vineyard and D.J. Weinkauff J. Am. Chem. Soc. 97 (1975), p. 2567. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (114)
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W. Oppolzer, C. Chapuis and G. Bernardinelli Helv. Chim. Acta 67 (1984), p. 1397. Full Text via CrossRef

The acid chlorides to were prepared by conjugate addition of R¹₂CuLi or R¹Li·CuI to methyl 2-butynoate ⁴, followed by saponification (NaOH, aq. MeOH, r.t.) and treatment with oxalyl chloride, benzene, r.t.. Acid chlorides and were obtained by treatment of the corresponding acids ⁵ with oxalyl chloride.

E.J. Corey and J.A. Katzenellenbogen J. Am. Chem. Soc. 91 (1969), p. 1851. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (66)
R.J. Anderson, V.L. Corbin, G. Cotterrell, G.R. Cox, C.A. Henrick, F. Schaub and J.B. Siddall J. Am. Chem. Soc. 97 (1975), p. 1197. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (21)

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D. Valentine, Jr., R.C. Sun and K. Toth J. Org. Chem. 45 (1980), p. 3703. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (1)

All new compounds were characterized by ¹H-NMR (360 MHz), IR and MS.

For the hydrogenation of non-functionalized alkenes with LiAlH₄/CoCl₂ see: E.G. Ashby and J.J. Lin J. Org. Chem 43 (1978), p. 2567. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (3)

R.H. Crabtree, H. Feikin, T. Fillebeen-Khan and G. Morris J. Organomet. Chem. 168 (1979), p. 183. Abstract | PDF (961 K) | View Record in Scopus | Cited By in Scopus (60)

A solution of (0.1 mmol) in anhydr. EtOH (5ml) containing 10% Pd on activated charcoal (13mg, Fluka) was shaken under H₂ using a Parr hydrogenator.

see also , , ¹¹ , , ⁵. H.B. Kagan and G. Thieme, Editors, Stereochemistry, Fundamentals and Methods 4 (1977) Reported [α]_D-values: .

W. Oppolzer, R. Moretti, T. Godel, A. Meunier and H. Löher Tetrahedron Lett. 24 (1983), p. 4971. Abstract | PDF (237 K) | View Record in Scopus | Cited By in Scopus (15)

W.H. Pirkle and J.R. Hauske J. Org. Chem. 42 (1977), p. 1839. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (14)

The narrow limitations In the use of chiral catalysts are illustrated by the modestly enantioselective hydrogenations of (E)- and (Z)- 3,7-dimethylocta-2,6-dienoic acids ⁵ as well as of neral and citronellal ¹⁴. For an alternative asymmetric synthesis of β-substituted carboxylic acids see ¹¹ and ¹⁵.

T.-P. Dang, Aviron-Violet, Y. Colleville and J. Varagnat J. Hoi. Catalysis 16 (1982), p. 51. Abstract | PDF (466 K) | View Record in Scopus | Cited By in Scopus (8)

W. Oppolzer, P. Dudfield, T. Stevenson and T. Godel Helv. Chim. Acta 68 (1985), p. 212. Full Text via CrossRef

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 183-186

Result list | previous < 16 of 36 > next

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