Syntheses of C2-symmetric vicinal diamines derived from tartaric acid

Tetrahedron Asymmetry

Volumn 10, Issue 18, 1999, Pages 3559-3570

  Scheurer, Andreas ^a,b   Mosset, Paul ^a   Saalfrank, Rolf W ^b  

^a UNIV RENNES   (France)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; TARTARIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033461156     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00353-5     Document Type: Article

References (22)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993.
2. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993.
3. (a) Tomioka, K. Synthesis 1990, 541-549.
4. (b) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526.
5. (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
6. (b) Nantz, M. H.; Lee, D. A.; Bender, D. M.; Roohi, A. H. J. Org. Chem. 1992, 57, 6653-6657.
7. (c) Kotsuki, H.; Kuzume, H.; Gohda, T.; Fukuhara, M.; Ochi, M.; Oishi, T.; Hirama, M.; Shiro, M. Tetrahedron: Asymmetry 1995, 6, 2227-2236.
8. Scheurer, A.; Mosset, P.; Saalfrank, R. W. Tetrahedron: Asymmetry 1997, 8, 1243-1251 and 3161.
9. Seebach, D.; Kalinowski, H.-O.; Bastani, B.; Crass, G.; Daum, H.; Dörr, H.; DuPreez, N. P.; Ehrig, V.; Langer, W.; Nüssler, C.; Oei, H.-A.; Schmidt, M. Helv. Chim. Acta 1977, 60, 301-325.
10. Diols 4a and 4b are commercially available [for a synthesis of 4a, see: Mash, E. A.; Nelson, K. A.; Van Deusen, S.; Hemperly, S. B. Org. Synth., Coll. Vol. VIII 1993, 155-161]. Diol 4c was used for diastereoselective cyclopropanations
11. [see: Mash, E. A.; Hemperly, S. B.; Nelson, K. A.; Heidt, P. C.; Van Deusen, S. J. Org. Chem. 1990, 55, 2045-2055].
12. However, the experimental and spectroscopic data of 4c were not reported. 4c was prepared from 2,3-O-isopropylidene-L-threitol [2,3-O-Isopropylidene-L-threitol is readily available from (+)-diethyl tartrate in two steps. We used the procedure described by Holy, A. (Collect. Czech. Chem. Commun. 1982, 47, 173-189; acetalization by triethyl orthoformate and acetone followed by reduction of the ethyl ester groups by sodium borohydride in absolute ethanol)] by double alkylation with 2-(bromomethyl)naphthalene followed by acetonide cleavage (see Experimental).
13. 60 affording chiral bisazafulleroids, see: Shen, C. K.-F.; Chien, K.-M.; Juo, C.-G.; Her, G.-R.; Luh, T.-Y. J. Org. Chem. 1996, 61, 9242-9244.
14. 4 resulted in cleavage of β-naphthylmethoxy groups to 2-methylnaphthalene. Use of other reducing agents (ammonium formate, Pd/C, MeOH or sodium borohydride in the presence of copper sulfate) led to complete decomposition.
15. The catalytic hydrogenation of diazide 6c to afford diamine 3c was also successful in isopropanol at 45°C, but THF was found to be more convenient. The catalytic hydrogenation of diazide 6a to diamine 3a was carried out in methanol, see Ref. 4, but THF is also an excellent solvent.
16. 3N, cat. DMAP, refluxing THF) only afforded a very low yield of 6d (14%).
17. Hanessian, S.; Staub, A. P. A. Tetrahedron Lett. 1973, 3555-3558.
18. In this case, palladium on carbon was a totally ineffective catalyst. However, when Pearlman's catalyst was used, diamine 6d was contaminated by colloidal palladium, which could not be removed.
19. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
20. Hanessian, S.; Lavallée, P. Can. J. Chem. 1975, 53, 2975-2977.
21. Recently, the vicinal diamines 3a-d were used for the preparation of salen Mn(III) complexes as catalysts for the enantioselective epoxidation of unfunctionalized alkenes: Scheurer, A.; Mosset, P.; Spiegel, M.; Saalfrank, R. W. Tetrahedron 1999, 55, 1063-1078.
22. Crude acetonide 8 was obtained along with residual 2-(bromomethyl)naphthalene and was used as such for the next step. Subsequent acetonide cleavage yielded crystalline diol 4c which was easily purified.