Synthesis and resolution of axially chiral C2-symmetric 1,1'-binaphthyl-substituted tetramethylethylenediamines

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2709-2721

  Mazaleyrat, Jean Paul ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENEDIAMINE; PUTRESCINE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030885779     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00301-7     Document Type: Article

References (20)

1. This work was done in the research group of Professor D. J. Cram at UCLA, during a post-doctoral research period from 1978 to 1980.
2. Mazaleyrat, J. P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585-4586.
3. Sogah, D. Y.; Cram, D. J. J. Am. Chem. Soc. 1985, 107, 8301-8302.
4. Rosini, C.; Tanturli, R.; Pertici, P.; Salvadori, P. Tetrahedron: Asymmetry 1996, 7, 2971-2982.
5. Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242-1251.
6. 11 for the reaction conducted in boiling DMF have been reported.
7. A practical synthesis of 1,1′-binaphthyl-2,2′-dicarboxylic acid from 2,2′-dimethyl-1,1′-binaphthyl was also developed. Brown, S. B.; Cram, D. J. unpublished results.
8. 9
9. Kanoh, S.; Hongoh, Y.; Motoi, M.; Suda, H. Bull. Chem. Soc. Jpn. 1988, 61, 1032-1034.
10. Yield based on the half-amount of starting racemic compound.
11. Colletti, S. L.; Halterman, R. L. Organometallies 1991, 10, 3438-3448.
12. Collet, A.; Brienne, M.-J.; Jacques, J. Bull. Soc. Chim. Fr., 1972, 127 and 336.
13. Tamao, K.; Minato, A.; Miyake, N.; Matsuda, T.; Kiso, Y.; Kumada, M. Chem. Lett. 1975, 133-136.
14. A detailed experimental procedure has been reported. Maigrot, N.; Mazaleyrat, J.-P. Synthesis 1985, 317-320.
15. Mazaleyrat, J. P.; Wakselman, M. J. Org. Chem., 1996, 61, 2695-2698.
16. 4
17. Optical rotations of the diamines 1 and 2 were always determined on samples being previously dried under vacuum (0.1 mm) at 110°C (refluxing toluene) for several hours.
18. Fitts, D. D.; Siegel, M.; Mislow, K. J. Am. Chem. Soc. 1958, 80, 480-486.
19. Racemic (RS)-1 is insoluble in dilute aqueous HC1 (giving a gel-like precipitate) but is well soluble in 37% HC1 (giving a clear yellow solution), whereas (-)-(R)-1 or (+)-(S)-1 are well soluble in both dilute and concentrated HC1. The hydrochloride salts of (RS)-2, (RS, SR)-2 and (-)-(R, R)-2 are all insoluble in both dilute and concentrated HC1.
20. 2O.