Stereoselective synthesis of functionalized 1,3 diols through the tandem isomerization-aldolization reaction mediated by nickel catalysts

Tetrahedron Letters

Volumn 47, Issue 44, 2006, Pages 7745-7748

  Petrignet, Julien ^a   Roisnel, Thierry ^b   Grée, René ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; NICKEL;

ARTICLE; CATALYST; CHEMICAL REACTION; ISOMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33748966487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.125     Document Type: Article

References (20)

1. See for example:. O'Hagan D. Nat. Prod. Rep. 12 (1995) 1-32
2. Davies-Coleman M.T., and Garson M.J. Nat. Prod. Rep. 15 (1998) 477-493
3. Rohr J. Angew. Chem., Int. Ed. 39 (2000) 2847-2849 and references cited therein
4. For general reviews on the aldol reactions see:. In: Heathcock C.H. (Ed). Comprehensive Organic Chemistry, Addition to C-X π Bonds, Part 2 (1991), Pergamon Press 99-319
5. In: Mahrwald R. (Ed). Modern Aldol Reactions (2004), Wiley-VCH, Weinheim, Germany and references cited therein
6. Crevisy C., Wietrich M., Le Boulaire V., Uma R., and Grée R. Tetrahedron Lett. 42 (2001) 395-398
7. Uma R., Davies M., Crevisy C., and Grée R. Tetrahedron Lett. 42 (2001) 3069-3072
8. Uma R., Gouault N., Crevisy C., and Grée R. Tetrahedron Lett. 44 (2003) 6187-6190
9. Cuperly D., Crevisy C., and Grée R. Synlett (2004) 93-96
10. Branchadell V., Crevisy C., and Grée R. Chem. Eur. J. 10 (2004) 5795-5803
11. Cuperly D., Petrignet J., Crévisy C., and Grée R. Chem. Eur. J. 12 (2006) 3261-3274
12. Alexakis A., Tranchier J.-P., Lensen N., and Mangeney P. J. Am. Chem. Soc. 117 (1995) 10767-10768
13. Alexakis A., and Mangeney P. In: Stephenson G.R. (Ed). Advances in Asymmetric Synthesis (1996), Chapman, London 93-110
14. Alexakis A., Mangeney P., Lensen N., Tranchier J.-P., Gosmini R., and Raussou S. Pure Appl. Chem. 68 (1996) 531-534
15. Cuperly D., Crevisy C., and Grée R. J. Org. Chem. 68 (2003) 6392-6399
16. The scope and limitations of the reaction, starting from 1, appear similar to those previously described for allylic alcohols bearing a bulky substituent in allylic position (Ref. 4b). Preliminary data (with non-optimized yields) indicate that the reaction can be performed with (i) substituted aromatic aldehydes such as p-fluorobenzaldehyde (59%) or p-methoxybenzaldehyde (35%), (ii) aliphatic aldehydes such as propionaldehyde (70%) or isobutyraldehyde (47%), or (iii) heterocyclic derivatives such as the challenging pyridine-2-carboxaldehyde (51%). The stereoselectivities are close to those observed with benzaldehyde and the corresponding results will be discussed in the full paper on this research.
17. The stereoselectivity of the isomerization-aldolization reaction, strongly in favor of the syn isomers, is in agreement with previous results in these series. A tentative explanation for the facial selectivity could be the following: as previously observed with bulky substituents at the carbinol center (see Ref. 4b) the isomerization could lead first to a Z enol, such as X, possibly stabilized by hydrogen bonding with the next imidazolidine nitrogen. Then reaction of the aldehyde from the less hindered side could afford aldols 5 and 7, while reaction on the other face of the enol would give aldol 6. Of course, other transition states are possible for these reactions and further studies will be necessary in order to fully rationalize this facial selectivity.{A figure is presented}
18. In: Smith M.B., and March J. (Eds). March's Advanced Organic Chemistry. 5th ed. (2001), John Wiley and Sons, New York 1401-1402
19. Petasis N.A., and Zavialov I.A. J. Am. Chem. Soc. 120 (1998) 11798-11799
20. Crystallographic data (excluding structure factors) for the structures in this letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 615450, CCDC 615451, CCDC 615452, CCDC 615453, CCDC 615454. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].