Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti’s base

Green Chemistry

Volumn 12, Issue 10, 2010, Pages 1747-1757

  Rosini, Goffredo ^a   Paolucci, Claudio ^a   Boschi, Francesca ^a   Marotta, Emanuela ^a   Righi, Paolo ^a   Tozzi, Francesco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HUMAN ECHOVIRUS 1;

EID: 78149458575     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c0gc00013b     Document Type: Article

References (103)

1. For authoritative monographs, see: Comprehensive Asymmetric Catalysis, ed., E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Heidelberg, 1996.
2. I. Ojima, Asymmetric Synthesis, VCH, Weinheim, 2nd ed., 2000.
3. M. Breuer K. Ditrich T. Habicher B. Hauer M. Kesseler R. Sturmer T. Zelinsky Angew. Chem., Int. Ed. 2004 43 788-824.
4. V. Farina J. T. Reeves C. H. Senanayake J. J. Song Chem. Rev. 2006 106 2734-2793.
5. S. Jaroch H. Weinmann K. Zeitler ChemMedChem 2007 2 1261-1264.
6. A. Dondoni A. Massi Angew. Chem., Int. Ed. 2008 47 2-25.
7. H. U. Blaser Chem. Commun. 2003 293 and literature cited therein.
8. H.-J. Federsel Nat. Rev. Drug Discovery 2005 4 685.
9. Asymmetric Catalysis on Industrial Scale, ed., H. U. Blaser, E. Schmidt, Wiley-VCH, Weinheim, 2004.
10. J. M. Hawkins T. J. N. Watson Angew. Chem., Int. Ed. 2004 43 3224-3228.
11. J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates, and Resolutions, Wiley & Sons, New York, 1981.
12. For a comprehensive survey of studies on this method for obtaining enantiopure compounds, see: CRC Handbook of Optical Resolutions via Diastereoisomeric Salt Formation, ed. David Kozma, CRC Press, London, 2001.
13. E. Fogassy M. Nógrádi D. Kozma G. Egri E. Pálovics V. Kiss Org. Biomol. Chem. 2006 4 3011.
14. F. Faigl E. Fogassy M. Nógrádi E. Pálovics J. Schindler Tetrahedron: Asymmetry 2008 19 519-536.
15. K. M. Brands A. J. Davies Chem. Rev. 2006 106 2711-2733.
16. N. G. Anderson Org. Process Res. Dev. 2005 9 800-813.
17. A common definition of “green chemistry” is “the design, development, and implementation of chemical processes and products to reduce or eliminate substances hazardous to human health and the environment” (P. T. Anastas and J. Warner, Green Chemistry Theory and Practice, Oxford Universirty Press, Oxford, 1998).
18. A more recent article expands this definition to twelve principles (M. Poliakoff J. M. Fittzpatrick T. R. Farren P. T. Anastas Science 2002 297 807.) reported also in.
19. National Research Council- Committee on Challenges for the Chemical Sciences in 21st Century, Beyond the Molecular Frontier- Challenges for Chemistry and Engineering Chemistry, The National Academy Press, Washington, D.C., 2003, pp 150–153, www.nap.edu.
20. In general, the CIDT methods concerning α-substituted carbonyl compounds rely upon well defined functional groups that intimately participate to the process. See the examples quoted in the Supporting Information Section of the reference 7.
21. J. Košmrlj L. O. Weigel D. A. Evans C. W. Downey J. Wu J. Am. Chem. Soc. 2003 125 3208-3209.
22. G. Rosini C. Ayoub V. Borzatta E. Marotta A. Mazzanti P. Righi Green Chem. 2007 9 441-448.
23. G. Rosini C. Ayoub V. Borzatta A. Mazzanti E. Marotta P. Righi Chem. Commun. 2006 4294-4296.
24. G. Rosini V. Borzatta F. Boschi G. Candido E. Marotta P. Righi Chem. Commun. 2007 2717-2719.
25. G. Rosini V. Borzatta C. Paolucci P. Righi Green Chem. 2008 10 1146-1151.
26. For a historical reports on the Betti reaction see: H. Wynberg J. Macromol. Sci., Part A: Pure Appl. Chem. 1989 A26 1033.
27. G. Rosini La Chim. e l’Ind. (Milan) 1999 81 231-238.
28. G. Rosini Atti Acc. Scienze detta dei XV, 121 2003 27-I 7-22.
29. For a review, see: I. Szatmári F. Fülöp Curr. Org. Synth. 2004 1 155-165.
30. In the past decade interest in the Betti base has intensified. This sort of “new life” for the Betti base derivatives is mainly due to the great interest they aroused as chiral non racemic ligands and auxiliaries in asymmetric synthesis (For selected references, see: C. Cardellicchio G. Ciccarella F. Naso E. Schingaro F. Scordari Tetrahedron: Asymmetry 1998 9 3667-3675.
31. C. Cardellicchio G. Ciccarella F. Naso F. Perna P. Tortorella Tetrahedron 1999 55 14685-14692.
32. G. Palmieri Tetrahedron: Asymmetry 2000 11 3361-3373.
33. D. Liu L. Zhang Q. Wang C. Da Z. Xin R. Wang M. C. K. Choi A. S. C. Chan Org. Lett. 2001 3 2733-2735.
34. C. Cimarelli A. Mazzanti G. Palmieri E. Volpini J. Org. Chem. 2001 66 4759-4765.
35. Y. Wang X. Li K. Ding Tetrahedron: Asymmetry 2002 13 1291-1297.
36. J. Ji L. Qiu C. W. Yip A. S. C. Chan J. Org. Chem. 2003 68 1589-1590.
37. J. Lu X. Xu C. Wang J. He Y. Hu H. Hu Tetrahedron Lett. 2002 43 8367-8369.
38. J. Lu X. Xu S. Wang C. Wang Y. Hu H. Hu J. Chem. Soc., Perkin Trans. 1 2002 2900-2903.
39. X. Xu J. Lu Y. Dong Y. Hu Synlett. 2004 122-124.
40. X. Xu J. Lu Y. Dong R. Li Z. Ge Y. Hu Tetrahedron: Asymmetry 2004 15 475-479.
41. Y. Dong J. Sun X. Wang X. Xu L. Cao Y. Hu Tetrahedron: Asymmetry 2004 15 1667-1672.
42. X. Wang Y. Dong J. Sun X. Xu R. Li Y. Hu J. Org. Chem. 2005 70 1897-1900.
43. For a very recent, excellent and authoritative review on Betti’s base and its history, see: C. Cardellicchio M. A. M. Capozzi F. Naso Tetrahedron: Asymmetry 2010 21 507-517.
44. Y. Dong R. Li J. Lu X. Xu X. Wang Y. Hu J. Org. Chem. 2005 70 8617.
45. The expressions “real world targets” and “real-life substrates” are referred to those products and intermediates that play a key role in the synthesis of chemicals currently exploited to solve some important problem of present days, by which there is a great interest, and therefore, an actual challenge to devise a more practical, efficient and economically convenient methodology to prepare them according to the green chemistry rules too.
46. Racemic Helional® (IFF), also named Tropional®, is a fragrance produced industrially via a cross-aldol condensation of piperonal and propanal followed by catalytic hydrogenation (K. Bauer, D. Garbe, H. Surburg, Common Fragrance and Flavor Materials, Wiley-VCH, 1997) with an annual production of about 300–350 tons.
47. Enders and Backes have published the first EPC synthesis of both enantiomers (ee = 90%) through the SAMP/RAMP hydrazone-alkylation strategy (D. Enders M. Backes Tetrahedron: Asymmetry 2004 15 1813-1817.) and described the olfactory evaluations and odour threshold values of each enantiomer.
48. Racemic Lilial® (Givaudan) is a lily-of-the-valley odorant and a precursor of the fungicide Fenpropimorph (W. Himmele, F.-Kohlmann, W. Herberle, German Patent, DE 2822326). Similarly to Helional® it is produced industrially via a cross-aldol condensation of 4-tert-butyl-benzaldehyde and propanal followed by hydrogenation (M. S. Carpenter, W. M. Jr Easter, U.S. Patent, 2,875,131, 1959, Givaudan).
49. The EPC synthesis of both enantiomers of Lilial has been performed exploiting the SAMP/RAMP methodology for enantioselective alkylation reactions (D. Enders H. Dyker Liebigs Ann. Chem. 1990 11 1107.).
50. Through the enantioselective hydrogenation of the corresponding unsaturated alcohol catalyzed by an iridium complex followed by oxidation (A. Lightfoot P. Schinder A. Pfaltz Angew. Chem., Int. Ed. 1998 37 2897.).
51. The hydrogenation of the corresponding unsaturated acid with a ruthenium complex incorporating (R)-BINAP followed by reduction (T. Yamamoto, in Current Topics in Flavours and Fragrances K. A. D. Swift, ed., Kluver Academic, Dordrech, The Nederlands1999, pp 33–38).
52. The fragrance Cyclamal was progressively substituted by the more stable Lilial®. Its preparation is very similar to those reported for the other α-methyl hydrocinnamic aldehydes and, to the best of our knowledge, no asymmetric synthesis of Cyclamal has been published.
53. L. A. Saudan Acc. Chem. Res. 2007 40 1309.
54. A. P. S. Narula Helv. Chim. Acta 2004 87 1992.
55. S. Lamboley C. Morel J. Y. De Saint Laumere A. F. Boshung N. G. J. Richards B. M. Winter Helv. Chim. Acta 2004 87 1767.
56. E. Brenna C. Fuganti S. Serra Tetrahedron: Asymmetry report N. 54 2003 14 1.
57. G. Frater J. A. Bajgrowikz P. Kraft Tetrahedron 1998 54 7633.
58. M. Betti, Organic Syntheses, Wiley & Sons: New York, 1941; Collect. Vol. 1, pp 381–383.
59. M. Betti Gazz. Chim. Ital. 1900 30-II 301-309.
60. 3 test for phenol convinced the Author, perhaps a pupil of Ugo Schiff, to prefer the structure of a Schiff base for the condensation product that underwent hydrochloric acid hydrolysis, thus changing the first assignment consisting into the 1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine structure (see Scheme 2). The same iminic structure was then assigned to the diastereoisomeric derivatives obtained by reaction of the enantiomers of 1-(α-aminobenzyl)-2-naphthol (1) with racemic aldehydes resolved by Betti.
61. M. Betti Gazz. Chim. Ital. 1903 33-I 17.
62. M. Betti J. Chem. Soc. 1903 84-I 510.
63. M. Betti V. Foa Gazz. Chim. Ital. 1903 33-I 27.
64. M. Betti V. Foa J. Chem. Soc. 1903 84-I 511.
65. M. Betti Atti Acc. Lincei 1930 11 587-593.
66. (Chem. Abstr. 1930, 24, 4473).
67. M. Betti P. Pratesi Atti Acc. Lincei 1930 11 646-649.
68. (Chem. Abstr. 1930, 24, 3771).
69. M. Betti P. Pratesi Ber. 1930 63B 874-5.
70. M. Betti P. Pratesi Biochem. Z. 1934 274 1-3.
71. (Chem. Abstr. 1935, 29, 733h).
72. H. E. Smith N. E. Cooper J. Org. Chem. 1970 35 2212-2215.
73. I. Szatmari T. A. Martinek L. Lazar F. Fülöp Tetrahedron 2003 59 2877.
74. −1, 230 nm, 20 °C.
75. For a discussion on the use of “% ee” and “% de” as expressions of stereoisomer composition, see: R. E. Gawley J. Org. Chem. 2006 71 2411.
76. a have been used in different concentrations in methanol. Among them we chose acetic acid in the reported concentrations in methanol to have a satisfying reaction rate avoiding a concomitant decomposition.
77. Renin is an important enzyme at the beginning of the renin angiotensin system (RAS), one of the key regulators of blood pressure. Efficient renin inhibitors decrease the plasma renin activity and reduce the production of angiotensin I from agiotensinogen.
78. The team of scientists (Novartis Institutes of Biomedical Research, NIBR) who invented aliskiren have been named Heroes of Chemistry 2009; Chem. Eng. News September 21, 2009, 46.
79. H. Rüeger S. Stutz R. Göschke F. Spindler J. Maibaum Tetrahedron Lett. 2000 41 10085-10089.
80. D. A. Sandham R. J. Taylor J. S. Carey A. Fässler Tetrahedron Lett. 2000 41 10091-10094.
81. A. Dondoni G. De Lathauwer D. Perrone Tetrahedron Lett. 2001 42 4819-4823.
82. R. R. Göschke S. Stutz W. Heinzelmann J. Maibaum Helv. Chim. Acta 2003 86 2848-2870.
83. H. Dong Z.-L. Zhang J.-H. Huang R. Ma S.-H. Chen G. Li Tetrahedron Lett. 2005 46 6337-6340.
84. K. B. Lindsay T. Skrydstrup J. Org. Chem. 2006 71 4766-4777.
85. H.-U. Blaser B. Pugin F. Spindler M. Thommen Acc. Chem. Res. 2007 40 1240-1250.
86. J. A. F. Boogers U. Felfer M. Koohaus L. Lefort G. Steinbauer A. H. M. de Vries J. G. de Vries Org. Process Res. Dev. 2007 11 585-591.
87. J. G. de Vries L. Lefort Chem.–Eur. J. 2006 12 4722-4734.
88. P. M. Jackson, I. C. Lennon and M. E. Fox, US Patent 2009/0099358 A1, applicant Dow Global Technologies Inc., 2009.
89. WO 2007/123957 A2, 2007.
90. W. Chen, F. Spindler and B. Pugin, WO 2007116081 A1, applicant Solvias AG, 2007.
91. T. Strurm W. Weissensteiner F. Spindler Adv. Synth. Catal. 2003 345 160-164.
92. P. Herold and S. Stutz, WO 2002002500 A1, assigned to Speedel Pharma AG, 2002.
93. N. Andrusko V. Andrusko T. Thyrann G. König A. Börner Tetrahedron Lett. 2008 49 5980-5982.
94. M. Betti, Organic Syntheses, Wiley & Sons: New York, Coll. Vol. 1, (1941), pp 381–383.
95. Y. Dong R. Li J. Lu X. Xu X. Wang Y. Hu J. Org. Chem. 2005 70 8617-8620.
96. P. Herold and S. Stutz, PCT WO 02/02500 A1 for Speedel Pharma AG.
97. 6) of (1S,3R,3S)-3e isomer δ: 159.0, 154.2, 144.2, 134.6, 133.2, 131.1, 130.7, 130.0, 129.9, 129.5, 129.0, 127.9, 127.4, 124.1, 124.0, 120.5, 115.7, 114.8, 84.8, 55.4, 54.9, 51.5, 32.9, 28.5, 22.0, 20.8.
98. R = 8.42) ratio. The methanol–AcOH filtrate showed a (1S,3R, R)/(1S,3R, R) = 64.8: 29.8 ratio.
99. Only the naphthoxazine 3f was completely soluble.
100. K. Kogami O. Takahashi J. Kumanotani Bull. Chem. Soc. Jpn. 1972 45 604-607.
101. A. Scrivanti M. Bertoldini V. Beghetto U. Matteoli Tetrahedron 2008 64 543-548.
102. A. Avdagić M. Gelo-Pujić V. Šunjić Synthesis 1995 1427-1431.
103. M. Kinoshita T. Miyake Y. Arima M. Oguma H. Akita Chem. Pharm. Bull. 2008 56 118-123.