The Betti base: Absolute configuration and routes to a family of related chiral nonracemic bases

Tetrahedron Asymmetry

Volumn 9, Issue 20, 1998, Pages 3667-3675

  Cardellicchio, Cosimo ^a   Ciccarella, Giuseppe ^a   Naso, Francesco ^a   Schingaro, Emanuela ^a   Scordari, Fernando ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHOL;

ARTICLE; CHIRALITY; ENANTIOMER; HYDROLYSIS; ISOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032561390     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00379-6     Document Type: Article

References (44)

1. Betti added methylmagnesium iodide to benzaldehyde in the presence of N,N-dimethylbornylamine, recording a small optical activity. (a) Betti, M.; Lucchi, E. Boll. Sci. Fac. Chim. Ind., Bologna, 1940, 1-2, 2-5. (Chem. Abstr. 1940, 34, 2354).
2. Betti added methylmagnesium iodide to benzaldehyde in the presence of N,N-dimethylbornylamine, recording a small optical activity. (a) Betti, M.; Lucchi, E. Boll. Sci. Fac. Chim. Ind., Bologna, 1940, 1-2, 2-5. (Chem. Abstr. 1940, 34, 2354).
3. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. Although the result was questioned (Tarbell, D. S.; Paulson, M. C. J. Am. Chem. Soc. 1942, 64, 2842-2844), it is worth emphasizing the seminal character of the original idea. Betti also performed some reactions in the presence of d- or l-polarized light.
5. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. Although the result was questioned (Tarbell, D. S.; Paulson, M. C. J. Am. Chem. Soc. 1942, 64, 2842-2844), it is worth emphasizing the seminal character of the original idea. Betti also performed some reactions in the presence of d- or l-polarized light.
6. (d) Betti, M.; Lucchi, E. Atti X Congr. Intern. Chim. 2 1938, 112-116. (Chem. Abstr. 1939, 33, 7273) and an asymmetric decomposition of a cyanohydrin with a chiral base.
7. (d) Betti, M.; Lucchi, E. Atti X Congr. Intern. Chim. 2 1938, 112-116. (Chem. Abstr. 1939, 33, 7273) and an asymmetric decomposition of a cyanohydrin with a chiral base.
8. (e) Betti, M.; Van Giffen, J. Gazz. Chim. Ital. 1912, 42 I, 316-320.
9. Betti, M. Gazz. Chim. Ital. 1900, 30 II, 310-316.
10. Betti, M. Gazz. Chim. Ital. 1901, 31 I, 377-393.
11. Betti, M. Gazz. Chim. Ital. 1901, 31 II, 170-184.
12. Betti, M. Gazz. Chim. Ital. 1901, 31 II, 191-200.
13. Betti, M. Gazz. Chim. Ital. 1903, 33 I, 1-17.
14. Betti, M. Gazz. Chim. Ital. 1903, 33 I, 17-26.
15. Betti, M. Gazz. Chim. Ital. 1903, 33 I, 27-35.
16. Betti, M. Gazz. Chim. Ital. 1904, 34 I, 213-223.
17. Betti, M. Gazz. Chim. Ital. 1906, 36 I, 388-401.
18. Betti, M. Organic Syntheses Collective 1941, 1, 381-383.
19. Smith, H. E.; Cooper, N. E. J. Org. Chem. 1970, 35, 2212-2215.
20. Pirrone, F. Gazz. Chim. Ital. 1936, 66, 518-524.
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23. Pirrone, F. Gazz. Chim. Ital. 1941, 71, 320-326.
24. Phillips, J. P.; Keown, R.; Fernando, Q. J. Am. Chem. Soc. 1953, 75, 4306-4307.
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27. Phillips, J. P. Chem. Rev. 1956, 56, 271-297.
28. Brode, W. R.; Littman, J. B. J. Am. Chem. Soc. 1930, 52, 1655-1659.
29. Betti, M. Gazz. Chim. Ital. 1906, 36 II, 392-394.
30. Betti, M. Gazz. Chim. Ital. 1906, 36 II, 666-669.
31. Betti, M.; Pratesi P. Ber. 1930, 63 B, 874-875.
32. Betti, M.; Pratesi P. Biochem. Z. 1934, 274, 1-3.
33. Betti, M. Gazz. Chim. Ital. 1912, 42 I, 288-294.
34. Desai, N. C.; Shukla, H. K.; Langalia, N. A.; Thaker, K. A. J. Ind. Chem. Soc. 1984, 61, 711-713 and references therein.
35. Grumbach, H. J.; Arend, M.; Risch, N. Synthesis 1996, 883-887.
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37. Ray, F. E.; Haefele, W. R. J. Am. Chem. Soc. 1938, 60, 36-38.
38. For example, Cainelli, G.; Giacomini, D.; Trerè, A.; Pilo Boyl, P. J. Org. Chem. 1996, 61, 5134-5139 and references therein.
39. Cardellicchio, C.; Ciccarella, G.; Naso, F. Italian Patent MI98A000159, of 29 January 1998.
40. Betti, M. Gazz. Chim. Ital. 1907, 37 I, 62-68.
41. North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Cryst. 1968, A24, 351-359.
42. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst. 1994, 27, 435.
43. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betterodge, P. W. Crystals Issue 10, 1996, Chemical Crystallography Laboratory.
44. Flack, H. D. Acta Cryst. 1983, A39, 876-881.