Asymmetric synthesis of 1- and 1,1'-ferrocenepropanoic acid

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7861-7864

  Locke, Andrew J ^a   Richards, Christopher J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030597046     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01751-0     Document Type: Article

References (15)

1. 1. Locke, A. J.; Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron, 1996, 52, 1461.
2. 2 Wright, J.; Frambes, L.; Reeves, P. J. Organomet. Chem., 1994, 476, 215.
3. 3. Schwink, L.: Knochel, P. Tetrahedron Lett., 1996, 37, 25.
4. 4. Experimental methods for methanolysis, silyl ketene acetal addition and ester hydrolysis are as previously described in reference 1.
5. 5. The previous synthesis of non-racemic 2a used resolved (R)-N,N-dimethyl-1-ferrocenylethylamine followed by quaternisation and treatment with wet acetonitrile, Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem., 1972, 37, 3052.
6. 3)Ph). Corresponding peaks for minor diastereoisomer, 2.69 (dd, J 15.1, 4.7), 5.87 (s).
7. 3)Ph). Corresponding peak for minor diastereoisomer, 5.80 (s).
8. 3)Ph). Corresponding peaks for minor diastereoisomer, 3.56 (s), 5.82 (s).
9. 3)Ph). Corresponding peaks for minor diastereoisomer, 3.57 (s), 5.80 (s).
10. 10. a) Hill, E. A.; Richards, J. H. J. Am. Chem. Soc., 1961, 83, 4216.
11. b) Ratajczak, A.; Misterkiewicz, B. J. Organomet. Chem., 1975, 91, 73.
12. c) For an exception due to the influence of other elements of chirality within a molecule see, Malezieux, B.; Gruselle, M.; Troitskaya, L. L.; Sokolov, V. I.; Vaissermann, J. Organometallics, 1994, 13, 2979.
13. 11. Davies, S. G.; Donohoe, T. J. Synlett, 1993, 323.
14. 3)Ph. Corresponding peak for minor diastereoisomer, 5.77 (s).
15. 2 chromatography as this promotes cyclisation to the meso 7-oxa[3]-ferrocenophane.