Intramolecular propargylic reduction in γ-benzyl protected Co2(CO)6- α,γ-acetylenic diols under Nicholas reaction conditions

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 743-746

  Díaz, David ^a   Martín, Víctor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Alkynes; Cobalt; Cobalt compounds; Nicholas reaction

Indexed keywords

BENZYL DERIVATIVE; COBALT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; REDUCTION;

EID: 0342514704     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02122-X     Document Type: Article

References (17)

1. Betancort, J. M.; Rodríguez, C. M.; Martín, V. S. Tetrahedron Lett. 1998, 39, 9773.
2. (a) Jacobi, P. A.; Murphree, S.; Rupprecht, F.; Zheng, W. J. Org. Chem. 1996, 61, 2413.
3. (b) Palazón, J. M.; Martín, V. S. Tetrahedron Lett. 1995, 36, 3549.
4. (c) Isobe, M.; Yenjai, C.; Tanaka, S. Synlett 1994, 916.
5. (d) Mukai, C.; Hanaoka, M. Synlett 1996, 11.
6. (e) Mukai, C.; Sugimoto, Y.; Miyazawa, K.; Yamaguchi, S.; Hanaoka, M. J. Org. Chem. 1998, 63, 6281.
7. Soler, M.; Martín, V. S. Tetrahedron Lett. 1999, 40, 2815.
8. Chiral 2,3-epoxy alcohols were regioselectively opened to the corresponding 1,3-diols. Benzylidene protection and regioselective reduction provided the secondary benzyl ether 2. Oxidation of the primary alcohol furnished the aldehyde that after lithium acetylide addition yielded 3.
9. For other examples of 'ionic hydrogenations' of alcohols, see: (a) Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis 1974, 633, and references cited therein.
10. (b) Adlington, M. G.; Orfanopoulos, M.; Fry, J. L. Tetrahedron Lett. 1976, 2955.
11. (c) Carey, F. A.; Tremper, H. S. J. Org. Chem. 1971, 36, 758.
12. (d) Olah, G. A.; Arvanaghi, M.; Ohannecian, L. Synthesis 1987, 770.
13. (e) Smonou, I.; Orfanopoulos, M. Tetrahedron Lett. 1988, 29, 5793, and references cited therein.
14. Nicholas, K. M.; Siegel, J. J. Am. Chem. Soc. 1985, 107, 4999.
15. Satisfactory spectroscopic data and combustion analyses were obtained for all new compounds.
16. Compound 6 was obtained by a similar sequence to that outlined in Scheme 2 using (3S,2R)-(hydroxymethyl)perhydro-2H-pyran-3-ol as the 1,3-diol. See: Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666.
17. We have isolated and characterised the benzaldehyde produced.