Application of menthol synthetic chemistry

Chemical Reviews

Volumn 107, Issue 5, 2007, Pages 2136-2164

  Oertling, Heiko ^a   Reckziegel, Aurélia ^a   Surburg, Horst ^a   Bertram, Heinz Juergen ^a  

^a SYMRISE AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ORGANIC CHEMICALS; SYNTHESIS (CHEMICAL);

MENTHOL; ORGANIC SYNTHESIS; SYNTHETIC CHEMISTRY;

CHEMISTRY;

EID: 34249939814     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr068409f     Document Type: Review

References (280)

1. (a) Fleischer, J.; Bauer, K.; Hopp, R. Haarmann & Reimer, DE 2109456, 1971; Chem. Abstr. 1972, 77, 152393h.
2. (b) Akutagawa, S. Chirality in Industry; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley & Sons Ltd.: Chichester, 1992; p 313.
3. (c) Hopp, R. Riv. Ital. EPPOS, Numero Speciale 1996, 111.
4. (d) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, 1996; p 343.
5. For the biosynthesis see (e) Croteau, R. B.; Davis, E. M.; Ringer, K. L.; Wildung, M. R. Naturwissenschaften 2005, 92, 562.
6. (a) Surburg, H; Panten, J. Common Fragrance and Flavor Materials; Wiley-VCH: Weinheim, 2006; p 54.
7. (b) http://www.leffingwell.com.
8. For 8-phenylmenthol, see Fernandez, F.; Garcia-Mera, X.; Lopez, C; Rodriguez, G.; Rodriguez-Borges, J. E. Tetrahedron: Asymmetry 2000, 11, 4805 and references cited therein.
9. Corey, E. J.; Carpino, P. J. Am. Chem. Soc. 1989, 111, 5472.
10. Martel, J.; Tessier, J.; Demoute, J.-P. Eur. Pat. Appl. EP-B 23454, 1981; Chem. Abstr. 1981, 95, 24788a.
11. (a) Moradei, O. M.; Paquette, L. A.; Peschko, C.; Danheiser, R. L. Org. Synth. 2003, 80, 66.
12. (b) Marinkovic, S.; Brule, C.; Hoffmann, N.; Prost, E.; Nuzillard, J.-M.; Bulach, V. J. Org. Chem. 2004, 69, 1646.
13. (c) Feringa, B. L.; de Lange, B.; de Jong, J. C. J. Org. Chem. 1989, 54, 2471.
14. (d) Feringa, B. L.; de Jong, J. C. Bull. Soc. Chim. Belg. 1992, 101, 7, 627.
15. (a) Chen, Q.; Geng, Z.; Huang, B. Tetrahedron: Asymmetry 1995, 6, 401.
16. (b) Huang, H.; Chen, Q. Tetrahedron: Asymmetry 1998, 9, 4103.
17. (c) Huang, H.; Chen, Q. Tetrahedron: Asymmetry 1999, 10, 1295.
18. (d) Fan, X.; Huang, M.; Huang, H.; Chen, Q. Chin. J. Chem. 2004, 22, 1359.
19. See also (e) Martin, M. R.; Mateo, A. I. Tetrahedron: Asymmetry 1994, 5, 1385.
20. Lee, N.; Kim, Y.-W.; Chang, K.; Kim, K. H.; Jew, S.-S.; Kim, D.-K. Tetrahedron Lett. 1996, 37, 2429.
21. (a) Feringa, B. L.; de Jong, J. C. J. Org. Chem. 1988, 53, 1125.
22. (b) de Jong, J. C.; Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron Lett. 1990, 31, 3047.
23. (c) de Jong, J. C.; van Bolhuis, F.; Feringa, B. L. Tetrahedron: Asymmetry 1991, 2, 1247.
24. (a) Paquette, L. A.; Moradei, O. M.; Bernardelli, P.; Lange, T. Org. Lett. 2000, 2, 1875.
25. (b) Bernardelli, P.; Moradei, O. M.; Friedrich, D.; Yang, J.; Gallou, F.; Dyck, B. P.; Doskotch, R. W.; Lange, T.; Paquette, L. A. J. Am. Chem. Soc. 2001, 123, 9021.
26. (a) Jauch, J. Angew. Chem., Int. Ed. 2000, 39, 2764.
27. (b) Jauch, J. Eur. J. Org. Chem. 2001, 473.
28. (c) Jauch, J. Synlett 2001, 1, 87.
29. Bush, E. J.; Jones, D. W. J. Chem. Soc., Perkin Trans. 1 1996, 151.
30. Robertson, J.; Menard, M.; Ford, R.; Bell, S. Org. Biomol. Chem. 2004, 2, 2988.
31. Mulzer, J.; Riether, D. Tetrahedron Lett. 1999, 40, 6197.
32. Ishibashi, F.; Park, S.; Kusano, T.; Kuwario, K. Biosci. Biotechnol. Biochem. 2005, 69, 291.
33. (a) Kang, F.-A.; Yu, Z.-Q.; Yin, H.-Y.; Yin, C.-L. Tetrahedron: Asymmetry 1997, 8, 3591.
34. (b) Geertsema, E. M.; Leung, C. W.; van Oeveren, A.; Meetsma, A.; Feringa, B. L. Tetrahedron Lett. 1995, 36, 7315.
35. For a detailed discussion of the addition of ethyl nitroacetate, see (c) Kang, F.-A.; Yin, C. L.; She, S.-W. J. Org. Chem. 1996, 61, 5523.
36. (a) Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron Lett. 1991, 32, 3239.
37. (b) van Oeveren, A.; Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1994, 59, 5999.
38. (a) Pelter, A.; Ward, R. S.; Jones, D. M.; Maddocks, P. J. Chem. Soc., Perkin Trans. 1 1993, 2621.
39. (b) Pelter, A.; Ward, R. S.; Jones, D. M.; Maddocks, P. J. Chem. Soc., Perkin Trans. 1 1993, 2631.
40. Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron: Asymmetry 1990, 1, 719.
41. (a) de Lange, B.; van Bolhuis, F.; Feringa, B. L. Tetrahedron 1989, 45, 6799.
42. (b) Feringa, B. L.; de Lange, B. Tetrahedron Lett. 1988, 29, 1303.
43. (c) Lubben, M.; Feringa, B. L. Tetrahedron: Asymmetry 1991, 2, 775.
44. Hulst, R.; de Vries, N. K.; Feringa, B. L. J. Org. Chem. 1994, 59, 7453.
45. He, L.; Liu, Y.; Zhang, W.; Li, M.; Chen, Q. Tetrahedron 2005, 61, 8505.
46. Jauch, J. J. Org. Chem. 2001, 66, 609.
47. (a) Jansen, J. F. G. A.; Feringa, B. L. Synth. Commun. 1992, 22, 1367.
48. For further examples concerning sulfur additions, see also (b) Feringa, B. L.; de Lange, B. Tetrahedron 1988, 44, 7213.
49. (c) de Jong, J. C.; van den Berg, K. J.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1991, 32, 7751.
50. (d) Garcia Ruano, J. L.; Bercial, F.; Fraile, A.; Martin Castro, A. M.; Martin, M. R. Tetrahedron: Asymmetry 2000, 11, 4737.
51. (a) Kang, F.-A.; Yin, C.-L. Tetrahedron 1998, 54, 13155.
52. See also (b) Zhang, X.; Huang, H.-H.; Chen, Q.-H. J. Asian Nat. Prod. Res. 2005, 7, 711.
53. See also ref 16a.
54. Sundermann, B.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 1995.
55. (a) Rispens, M. T.; Keller, E.; de Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607.
56. (b) de Lange, B.; Feringa, B. L. Tetrahedron Lett. 1988, 29, 5317.
57. (a) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791.
58. (b) Dondas, H. A.; Grigg, R.; Thornton-Pett, M. Tetrahedron 1996, 52, 13455.
59. (c) Dondas, H. A.; Grigg, R.; Kilner, C. Tetrahedron 2003, 59, 8481.
60. Hoffmann, N. Tetrahedron: Asymmetry 1994, 5, 879.
61. (a) Bertrand, S.; Glapski, C.; Hoffmann, N.; Pete, J.-P. Tetrahedron Lett. 1999, 40, 3169.
62. (b) Bertrand, S.; Hoffmann, N.; Humbel, S.; Pete, J.-P. J. Org. Chem. 2000, 65, 8690.
63. (a) Bertrand, S.; Hoffmann, N.; Pete, J.-P. Tetrahedron Lett. 1999, 40, 3173.
64. (b) Bertrand, S.; Hoffmann, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227.
65. Bertrand, S.; Hoffmann, N.; Pete, J.-P.; Bulach, V. Chem. Commun. 1999, 2291.
66. (a) Hoffmann, N.; Scharf, H. D.; Runsink, J. Tetrahedron Lett. 1989, 30, 2637.
67. (b) Hoffmann, N.; Scharf, H. D. Liebigs Ann. Chem. 1991, 1273.
68. (c) Curtius, F. W.; Scharf, H. D. Tetrahedron: Asymmetry 1996, 7, 2957.
69. Bertrand, S.; Hoffmann, N.; Pete, J. P. Tetrahedron 1998, 54, 4873.
70. Heywang, U.; Koppe, T.; Schwarz, M. WO 02/04460 Al, 2002; Chem. Abstr. 2002, 136, 102234y.
71. Krief, A.; Lecomte, P.; Demoute, J. P.; Dumont, W. Synthesis 1990, 275.
72. Bains, S.; Pagni, R. M.; Kabalka, G. W.; Pala, C. Tetrahedron: Asymmetry 1994, 5, 821.
73. (a) Vassen, R.; Runsink, J.; Scharf, H. D. Chem. Ber. 1986, 119, 3492.
74. (b) Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113.
75. (c) Donnelly, I. H.; Kambouris, P.; Nonhebel, D. C.; Rohr, T.; Sherrington, D. C. J. Chem. Soc., Perkin Trans. 2 1996, 1821.
76. (d) Kiesman, W. F.; Petter, R. C. Tetrahedron: Asymmetry 2002, 13, 957.
77. (a) Nozaki, K.; Yoshihara, M.; Matsubara, Y.; Maeshima, T. Phosphorus Sulfur 1985, 22, 1.
78. (b) Heathcock, C. H.; Davis, B. R.; Hadley, C. R. J. Med. Chem. 1989, 32, 197.
79. (c) Longbottom, D. A.; Morrison, A. J.; Dixon, D. J.; Ley, S. V. Tetrahedron 2003, 59, 6955.
80. (a) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
81. (b) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333.
82. (c) Furuta, K.; Iwanaga, K.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 4507.
83. Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross, C. R., II. Tetrahedron: Asymmetry 1997, 8, 3079.
84. Hamanaka, N.; Seko, T.; Miyazaki, T.; Naka, M.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 2399.
85. Longbottom, D. A.; Morrison, A. J.; Dixon, D. J.; Ley, S. V. Angew. Chem., Int. Ed. 2002, 41, 2786.
86. Solladié, G.; Lohse, O. J. Org. Chem. 1993, 58, 4555.
87. Corey, E. J.; Su, W.-G. Tetrahedron Lett. 1988, 29, 3423.
88. Karle, M.; Bockelmann, D.; Schumann, D.; Griesinger, C.; Koert, U. Angew. Chem., Int. Ed. 2003, 42, 4546 and supporting information.
89. Thunberg, L.; Allenmark, S. Tetrahedron: Asymmetry 2003, 14, 1317.
90. Winkler, J. D.; Piatnitski, E. L.; Mehlmann, J.; Kasparec, J.; Axelsen, P. H. Angew. Chem., Int. Ed. 2001, 40, 743.
91. (a) Schwenninger, R.; Ramondenc, Y.; Wurst, K.; Schlögl, J.; Kräutler, B. Chem. Eur. J. 2000, 6, 1214.
92. (b) Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907.
93. Ito, Y. N.; Ariza, X.; Beck, A. K.; Bohac, A.; Ganter, C.; Gawley, R. E.; Kühnle, F. N. M.; Tuleja, J.; Wang, Y. M.; Seebach, D. Helv. Chim. Acta 1994, 77, 2071.
94. (a) Ahmad, S. Tetrahedron Lett. 1991, 32, 6997.
95. (b) Brunner, A. Eur. Pat. Appl. EP 0893427 Bl, 2001; Chem Abstr. 1999, 130, 109976b.
96. De Vos, M. J.; Krief, A. Tetrahedron Lett. 1983, 24, 103.
97. Baskaran, S.; Baskaran, C.; Nadkarni, P. J.; Trivedi, G. K. Tetrahedron 1997, 53, 7057.
98. (a) Misumi, A.; Iwanaga, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343.
99. (b) Furuta, K.; Iwanaga, K.; Yamamoto, H.; Mori, I.; Heathcock, C. H. Org. Synth. 1989, 67, 76.
100. (a) Trost, B. M.; Dirat, O.; Gunzner, J. L. Angew. Chem., Int. Ed. 2002, 41, 841.
101. (b) Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396.
102. Fujiama, O.; Javier de la Mata, F.; Grubbs, R. H. Organometallics 1996, 15, 1865.
103. Izawa, T.; Ogino, Y.; Nishiyama, S.; Yamamura, S.; Kato, K.; Takita, T. Tetrahedron 1992, 48, 1573.
104. (a) Kende, A. S.; Fujii, Y.; Mendoza, J. S. J. Am. Chem. Soc. 1990, 112, 9645.
105. (b) Kende, A. S.; Mendoza, J. S.; Fujii, Y. Tetrahedron 1993, 49, 8015.
106. See also (c) Lee, E.; Choi, S. J.; Kim, H.; Han, H. O.; Kim, Y. K.; Min, S. J.; Son, S. H.; Lim, S. M.; Jang, W. S. Angew. Chem., Int. Ed. 2002, 41, 176.
107. (a) Hub, L.; Mosher, H. S. J. Org. Chem. 1970, 35, 3691.
108. See also (b) Blanco, J. M.; Caamano, O.; Fernandez, F.; Garcia-Mera, X.; Lopez, C.; Rodriguez-Borges, J. E.; Hergueta, A. R. Synthesis 1998, 1590.
109. (c) Ebeling, S. C.; Matthies, D. J. Prakt. Chem. 1994, 336, 271.
110. (d) Jurczak, J.; Zamojski, A. Rocz. Chem. 1970, 44, 2257.
111. (e) Fernandez, F.; Garcia, G.; Rodriguez, J. E. Synth. Commun. 1990, 20, 2837.
112. (a) Macquarrie, D. WO 96/22960, 1996; Chem Abstr. 1996, 125, 196056q.
113. For a similar approach, see also (b) Kloimstein, E.; Giselbrecht, K. H.; Hendel, W.; Perndorfer, E.; Reiter, K.; Burger, C.; Praus, A. EP 0844232 Al, 1997; Chem. Abstr. 1998, 129, 41285x.
114. Schouteeten, A. DE 4435647 Al, 1995; Chem Abstr. 1995, 123, 56326m.
115. (a) Goodyear, M. D.; Dwyer, O. P.; Hill, M. L.; Whitehead, A. J.; Hornby, R.; Hallett, P. WO 95/29174, 1995; Chem Abstr. 1996, 124, 146759e.
116. (b) Jin, H.; Siddiqui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S.; Goodyear, M. D.; Ravenscrok P.; Beels, C. D. J. Org. Chem. 1995, 60, 2621.
117. (c) Goodyear, M. D.; Hill, M. L.; West, J. P.; Whitehead, A. J. Tetrahedron Lett. 2005, 46, 8535.
118. (a) Wang, W.; Jin, H.; Mansour, T. S. Tetrahedron Lett. 1994, 35, 4739.
119. (b) Brossette, T.; Klein, E.; Creminon, C.; Grassi, J.; Mioskowski, C.; Lebeau, L. Tetrahedron 2001, 57, 8129.
120. (a) Achmatowicz, O., Jr.; Szechner, B. J. Org. Chem. 1972, 37, 964.
121. (b) Whitesell, J. K.; Bhattacharya, A.; Aguilar, D. A.; Henke, K. J. Chem. Soc., Chem. Commun. 1982, 989.
122. See also (c) Whitesell, J. K.; Lawrence, R. M.; Chen, H.-H. J. Org. Chem. 1986, 51, 4479.
123. (d) Rozners, E.; Liu, Y. J. Org. Chem. 2005, 70, 9841.
124. For a similar double asymmetric approach see: (e) Qian, C.; Wang, L. Tetrahedron: Asymmetry 2000, 11, 2347.
125. (a) Mulzer, J.; Meyer, F.; Buschmann, J.; Luger, P. Tetrahedron Lett. 1995, 36, 3503.
126. (b) Schmidt, R. R.; Abele, W. Angew. Chem., Int. Ed. Engl. 1982, 21, 302.
127. (a) Bigi, F.; Casnati, G.; Sartori, G.; Dalprato, C.; Bortolini, R. Tetrahedron: Asymmetry 1990, 1, 861.
128. (b) Bigi, F.; Bocelli, G.; Maggi, R.; Sartori, G. J. Org. Chem. 1999, 64, 5004.
129. (a) Matsumoto, K.; Harada, K. J. Org. Chem. 1966, 31, 1956.
130. (b) Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G.; Soncini, P.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett. 1985, 26, 2021.
131. (c) Piccolo, O.; Filippini, L.; Tinucci, L.; Valoti, E.; Citterio, A. Helv Chim. Acta 1984, 67, 739.
132. See also (d) Casiraghi, G.; Bigi, F.; Casnati, G.; Sartori, G.; Soncini, P.; Fava, G. G.; Belicchi, M. F. J. Org. Chem 1988, 53, 1779.
133. (e) Hauser, F. M.; Ganguly, D. J. Org. Chem. 2000, 65, 1842.
134. (f) Si, Y. G.; Chen, J.; Li, F.; Li, J. H.; Qin, Y. J.; Jiang, B. Adv. Synth. Catal. 2006, 348, 898.
135. For Grignard addition see (a) Prelog, V.; Meier, H. L. Helv. Chim. Acta 1953, 36, 320.
136. (b) Evans, R. J. D.; Landor, S. R. J. Chem. Soc. 1965, 2553.
137. For zinc-mediated addition see (c) Boireau, G.; Deberly, A.; Abenhaim, D. Tetrahedron 1989, 45, 5837.
138. (d) Esser, P.; Buschmann, H.; Meyer-Stork, M.; Scharf, H.-D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1190.
139. (e) Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449.
140. For cerium-mediated addition see (f) Luzzio, F. A.; Mayorov, A. V.; Menes, M. E. Nucleosides Nucleotides 1999, 18, 1977.
141. For aluminum-mediated addition see (g) Deberly, A.; Boireau, G.; Abenhaim, D. Tetrahedron Lett. 1984, 25, 655.
142. Rozema, M. J.; Kruger, A. W.; Rohde, B. D.; Shelat, B.; Bhagavatula, L.; Tien, J. J.; Zhang, W.; Henry, R. F. Tetrahedron 2005, 61, 4419.
143. Krasik, P. Tetrahedron Lett. 1998, 39, 4223.
144. Phillips, H. J. Chem. Soc. 1925, 127, 2552.
145. (a) Solladié, G.; Hutt, I.; Girardin, A. Synthesis 1987, 173.
146. (b) Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227.
147. (c) Solladié, G. Synthesis 1981, 185.
148. (d) Hulce, M.; Mallamo, J. P.; Frye, L. L.; Kogan, T. P.; Posner, G. H.; Clark, E. B.; Crevoisier, M.; Kang, H. Y.; Coates, R. M. Org. Synth. 1986, 64, 196.
149. (a) Klunder, J. M.; Sharpless, K. B. J. Org. Chem. 1987, 52, 2598.
150. For a modification of the procedure using triphenyl phosphine instead of trimethyl phosphite see (b) Watanabe, Y.; Mase, N.; Tateyama, M.; Toru, T. Tetrahedron: Asymmetry 1999, 10, 737.
151. (a) Andersen, K. K. Tetrahedron Lett. 1962, 93.
152. (b) Andersen, K. K.; Gaffield, W.; Papanikolaou, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem Soc. 1964, 86, 5637.
153. For improved yields with benzene as solvent see (c) Drabowicz, J.; Bujnicki, B.; Mikolajczyk, M. J. Org. Chem. 1982, 47, 3325.
154. (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
155. (b) Fernandez, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
156. (c) Pellissier, H. Tetrahedron 2006, 62, 5559.
157. (a) Solladié, G.; Wilb, N.; Bauder, C. Eur. J. Org. Chem. 1999, 3021.
158. (b) Solladié, G.; Gressot, L.; Colobert, F. Eur. J. Org. Chem. 2000, 357.
159. (c) Brinkmann, Y.; Carreño, M. C.; Urbano, A.; Colobert, F.; Solladié, G. Org. Lett. 2004, 6, 4335.
160. See also (d) Solladié, G.; Bauder, C. WO 97/19917, 1997; Chem. Abstr. 1997, 127, 81290k.
161. (a) Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
162. See also (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
163. (c) Paquette, L. A.; Tae, J.; Arrington, M. P.; Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742.
164. (a) Posner, G. H.; Mallamo, J. P.; Miura, K. J. Am. Chem Soc. 1981, 103, 2886.
165. (b) Posner, G. H.; Mallamo, J. P.; Hulce, M.; Frye, L. L. J. Am. Chem. Soc. 1982, 104, 4180.
166. (a) Girodier, L. D.; Maignan, C. S.; Rouessac, F. P. Tetrahedron: Asymmetry 1992, 3, 857.
167. (b) Girodier, L. D.; Maignan, C. S.; Rouessac, F. P. Tetrahedron: Asymmetry 1995, 6, 2045.
168. (a) Montana, A. M.; Grima, P. M. Tetrahedron 2002, 58, 4769.
169. (b) Montana, A. M.; Grima, P. M. Tetrahedron Lett. 2002, 43, 2017.
170. (a) Carreño, M. C.; Garcia Ruano, J. L.; Urbano, A. Synthesis 1992, 651.
171. For a very recent application of enantiomerically pure sulfinylquinones see (b) Lanfranchi, D. A.; Hanquet, G. J. Org. Chem. 2006, 71, 4854.
172. (a) Carreño, M. C.; Gonzalez-Lopez, M.; Urbano, A. Chem Commun. 2005, 611.
173. See also (b) Carreño, M. C.; Garcia-Cerrada, S.; Urbano, A. J. Am. Chem. Soc. 2001, 123, 7929.
174. (a) Houpis, I.; Molina, A.; Volante, R. P WO 97/38976, 1997; Chem. Abstr. 1998, 128, 3606z.
175. (b) Houpis, I. N.; Molina, A.; Dorziotis, I.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1997, 38, 7131.
176. Rebiere, F.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1990, 31, 3121.
177. (a) Guillaneux, D.; Kagan, H. B. J. Org. Chem 1995, 60, 2502.
178. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511.
179. (c) Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robben, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508.
180. (d) Priego, J.; Mancheno, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346.
181. (e) Cotton, H. K.; Huerta, F. F.; Bäckvall, J.-E. Eur. J. Org. Chem. 2003, 2756.
182. Rebiere, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568.
183. (a) Pedersen, H. L.; Johannsen, M. J. Org. Chem. 2002, 67, 7982.
184. (b) Argouarch, G.; Samuel, O.; Riant, O.; Daran, J.-C.; Kagan, H. B. Eur. J. Org. Chem. 2000, 2893.
185. See also (c) Priego, J.; Mancheno, O. G.; Cabrera, S.; Arrayas, R. G.; Llamas, T.; Carretero, J. C. Chem. Commun. 2002, 2512.
186. (d) Lotz, M.; Kramer, G.; Knochel, P. Chem. Comman. 2002, 2546.
187. (e) Lotz, M,; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 4708.
188. (f) Kloetzing, R. J.; Knochel, P. Tetrahedron: Asymmetry 2006, 17, 116.
189. (g) Knochel, P.; Lotz, M.; Monsees, A.; Riermeier, T.; Kadyrov, R.; Almena, J. DE 10211250 A1 2003; Chem. Abstr. 2003, 139, 261423n.
190. For chiral DMAP-analogues see (h) Seitzberg, J. G.; Dissing, C.; Sotofte, I.; Norrby, P. O.; Johannsen, M. J. Org. Chem. 2005, 70, 8332.
191. For a recent application of this methodology see (i) Albrow, V. E.; Blake, A. J.; Fryatt, R.; Wilson, C.; Woodward, S. Eur. J. Org. Chem. 2006, 2549.
192. (a) Cinquini, M.; Cozzi, F. J. Chem. Soc, Chem. Commun. 1977, 502.
193. (b) Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc. Perkin Trans. 1 1982, 339.
194. For lithioimines see (c) Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4.
195. (a) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229.
196. (b) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D. L.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
197. (c) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
198. (d) Fanelli, D. L.; Szewczyk, J. M.; Zhang, Y.; Reddy, G. V.; Burns, D. M.; Davis, F. A.; Unch, J.; Hart, D. J. Org. Synth. 2000, 77, 50.
199. (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
200. (b) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
201. (c) Davis, F. A.; Yang, B.; Deng, J.; Zhang, J. ARKIVOC 2006, 120.
202. Storace, L.; Anzalone, L.; Confalone, P. N.; Davis, W. P.; Fortunak, J. M.; Giangiordano, M.; Haley, J. J., Jr.; Kamholz, K.; Li H.-Y.; Ma, P.; Nugent, W. A.; Parsons, R. L., Jr.; Sheeran, P. J.; Silverman, C. E.; Waltermire, R. E.; Wood, C. C. Org. Proc. Res. Dev. 2002, 6, 54.
203. DeGoey, D. A.; Chen, H.-J.; Flosi, W. J.; Grampovnik, D. J.; Yeung, C. M.; Klein, L. L.; Kempf, D. J. J. Org. Chem. 2002, 67, 5445.
204. Velazquez, F.; Arasappan, A.; Chen, K.; Sannigrahi, M.; Venkatraman, S.; McPhail, A. T.; Chan, T. M.; Shih, N. Y.; Njoroge, F. G. Org. Lett. 2006, 8, 789.
205. (a) Williams, T. R.; Nudelman, A.; Booms, R. E.; Cram, D. J. J. Am. Chem. Soc. 1972, 4684.
206. (b) Garcia-Ruano, J. L.; Alonso, R.; Zarzuelo, M. M.; Noheda, P. Tetrahedron: Asymmetry 1995, 6, 1133.
207. (c) Carreño, M. C.; Ribagorda, M. J. Org. Chem. 2000, 65, 1231.
208. (d) Gremmen, C.; Willemse, B.; Wanner, M. J.; Koomen, G.-J. Org. Lett. 2000, 2, 1955.
209. For enantioseparation of 2-piperidino benzylamines see (e) Grell, W.; Hurnaus R.; Griss, G.; Sauter, R.; Rupprecht, E.; Mark, M.; Luger, P.; Nar, H.; Wittneben, H.; Müller, P. J. Med. Chem. 1998, 41, 5219.
210. (a) Cherkaoui, M. Z.; Nicoud, J. F. New J. Chem. 1995, 19, 851.
211. (b) Capozzi, M. A. M.; Cardellicchio, C.; Naso, F.; Spina, G.; Tortorella, P. J. Org. Chem. 2001, 66, 5933.
212. For a 50 g synthesis of menthyl o-bromobenzenesulfinate according to Solladiés method see (c) Imboden, C.; Renaud, P. Tetrahedron: Asymmetry 1999, 10, 1051.
213. Capozzi, M. A. M.; Cardellicchio, C.; Naso, F. Eur. J. Org. Chem. 2004, 1855.
214. Pochetti, G.; Gavuzzo, E.; Campestre, C.; Agamennone, M.; Tortorella, P.; Consalvi, V.; Gallina, C.; Hiller, O.; Tschesche, H.; Tucker, P. A.; Mazza, F. J. Med. Chem. 2006, 49, 923.
215. (a) Smith, J. G.; Wright, G. F. J. Org. Chem. 1952, 17, 1116.
216. See also (b) Procter, D. J.; Thornton-Pett, M.; Rayner, C. M. Tetrahedron 1996, 52, 1841.
217. (c) Senaratne, K. P. A.; Orihuela, F. M.; Malcolm, A. J. WO 98/49100, 1998; Chem. Abstr. 1999, 130, 3969m.
218. 3, see (d) Hückel, W.; Pietrzok, H. Justus Liebigs Ann. Chem. 1939, 540, 250.
219. (e) Cunningham, D.; Gallagher, E. T.; Grayson, D. H.; McArdle, P. J.; Storey, C. B.; Wilcock, D. J. J. Chem. Soc., Perkin Trans. 1 2002, 2692.
220. (a) Horner, L.; Oediger, H.; Hoffmann, H. Justus Liebigs Ann. Chem. 1959, 626, 26.
221. For neomenthyl chloride from menthyl chloroformate, see (b) Bestmann, H. J.; Schnabel, K. H. Justus Liebigs Ann. Chem. 1966, 698, 106.
222. For a detailed stereomechanistic discussion see (a) Beckmann, J.; Dakternieks, D.; Dräger, M.; Duthie, A. Angew. Chem., Int. Ed. 2006, 45, 6509.
223. (b) Krause, H. W.; Kinting, A. J. Prakt. Chem. 1980, 322, 485.
224. (c) Vedejs, E.; Donde, Y. J. Org. Chem. 2000, 65, 2337.
225. (d) Brunner, H.; Störiko, R.; Nuber, B. Tetrahedron: Asymmetry 1998, 9, 407.
226. (e) Cui, X-L.; Brown, R. S. J. Org. Chem. 2000, 65, 5653.
227. (f) Rowsell, D. G. GB 1392907, 1975; Chem. Abstr. 1975, 83, 114682t.
228. (a) Morrison, J. D.; Masler, W. F. J. Org. Chem. 1974, 39, 270.
229. (b) Tanaka, M.; Ogata, I. Bull. Chem. Soc. Jpn. 1975, 48, 1094.
230. (c) Aguiar, A. M.; Morrow, C. J.; Morrison, J. D.; Burnett, R. E.; Masler, W. F.; Bhacca, N. S. J. Org. Chem. 1976, 41, 1545.
231. (d) Honaker, M. T.; Sandefur, B. J.; Hargett, J. L.; McDaniel, A. L.; Salvatore, R. N. Tetrahedron Lett. 2003, 44, 8373.
232. (a) Morrison, J. D.; Burnett, R. E.; Aguiar, A. M.; Morrow, C. J.; Philipps, C. J. Am. Chem. Soc. 1971, 93, 1301.
233. (b) Valentine, D., Jr.; Johnson, K. K.; Priester, W.; Sun, R. C.; Toth, K.; Saucy, G. J. Org. Chem. 1980, 45, 3698.
234. (a) Kiso, Y.; Yamamoto, K.; Tamao, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4373.
235. (b) Kawashima, Y.; Okano, K.; Nozaki, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 2004, 77, 347.
236. (a) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442.
237. (b) Luanphaisarnnont, T.; Ndubaku, C. O.; Jamison, T. F. Org. Lett. 2005, 7, 2937.
238. (a) Meth-Cohn, O. J. Chem. Soc., Chem. Commun. 1986, 695.
239. See also (b) Meth-Cohn, O.; Zenchoff, G.; Maehr, H.; Coffen, D. Org. Synth. 1990, 68, 155.
240. (a) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418.
241. (b) Lee-Ruff, E.; Xi, F.-D.; Qie, J. H. J. Org. Chem. 1996, 61, 1547.
242. (c) Sukopp, M.; Schwab, R.; Marinelli, L.; Biron, E.; Heller, M.; Varkondi, E.; Pap, A.; Novellino, E.; Keri, G.; Kessler, H. J. Med. Chem. 2005, 48, 2916.
243. Marvel, C. S.; Frank, R. L. J. Am. Chem. Soc. 1942, 64, 1675.
244. Adair, G. R. A.; Edwards, M. G.; Williams, J. M. J. Tetrahedron Lett. 2003, 44, 5523.
245. (a) Corey, E. J.; Easley, H. E. J. Am. Chem. Soc. 1975, 97, 6909.
246. (b) Oppolzer, W.; Kurth, M.; Reichlin, D.; Moffatt, F. Tetrahedron Lett. 1981, 22, 2545.
247. (c) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
248. (a) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475.
249. (b) Barr, D. A.; Dorrity, M. J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273.
250. (a) Cai, J.; Zhou, Z.; Zhao, G.; Tang, C. Org. Lett. 2002, 4, 4723
251. see also (b) He, K.; Zhou, Z.; Zhao, G.; Tang, C. Heteroat. Chem. 2006, 17, 317.
252. (a) Baldwin, J. E.; Carter, C. G. J. Am. Chem. Soc. 1982, 104, 1362.
253. (b) Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553.
254. (c) Krieger, P. E.; Landgrebe, J. A. J. Org. Chem. 1978, 43, 4447.
255. (a) Fritschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 1005.
256. (b) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599.
257. (c) Tepfenhart, D.; Moisan, L.; Dalko, P. I.; Cossy, J. Tetrahedron Lett. 2004, 45, 1781.
258. (a) Doyle, M. P.; Brandes, B. D.; Kazala, A. P.; Pieters, R. J.; Jarstfer, M. B.; Watkins, L. M.; Eagle, C. T. Tetrahedron Lett. 1990, 31, 6613.
259. (b) Doyle, M. P.; Protopopova, M. N.; Brandes, B. D.; Davies, H. M. L.; Huby, N. J. S.; Whitesell, J. K. Synlett 1993, 151.
260. (c) Hu, W.; Timmons, D. J.; Doyle, M. P. Org. Lett. 2002, 4, 901.
261. (a) Iwasa, S.; Takezawa, F.; Tuchiya, Y.; Nishiyama, H. Chem. Commun. 2001, 59.
262. (b) Iwasa, S.; Tsushima, S.; Nishiyama, K.; Tsuchiya, Y.; Takezawa, F.; Nishiyama, H. Tetrahedron: Asymmetry 2003, 14, 855.
263. (a) Goldberg, S. I.; Ragade, I. J. Org. Chem. 1967, 32, 1046.
264. (b) Westley, J. W.; Halpern, B. J. Org. Chem. 1968, 33, 3978.
265. (c) Harris, J. M.; Bolessa, E. A.; Mendonca, A. J.; Feng, S.-C.; Vederas, J. C. J. Chem. Soc., Perkin Trans. 1 1995, 1945.
266. (a) Goren, Z.; Heeg, M. J.; Mobashery, S. J. Org. Chem. 1991, 56, 7186.
267. (b) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397.
268. (c) Li, Z.; Liang, X.; Wu, F.; Wan, B. Tetrahedron: Asymmetry 2004, 15, 665.
269. For a procedure employing trichloromethyl chloroformate, see (d) Yamamoto, Y.; Nakada, T.; Nemoto, H. J. Am. Chem. Soc. 1992, 114, 121.
270. (a) Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1995, 60, 6599.
271. (b) Kolotuchin, S. V.; Meyers, A. I. J. Org. Chem. 1999, 64, 7921.
272. (c) Botman, P. N. M.; Postma, M.; Fraanje, J.; Goubitz, K.; Schenk, H.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2002, 1952.
273. (d) Yekta, S.; Krasnova, L. B.; Mariampillai, B.; Picard, C. J.; Chen, G.; Pandiaraju, S.; Yudin, A. K. J. Fluorine Chem. 2004, 125, 517.
274. (a) Aguilo, A.; Martin-Lomas, M.; Penades, S. Tetrahedron Lett. 1992, 33, 401.
275. (b) Martin-Lomas, M.; Flores-Mosquera, M.; Chiara, J. L. Eur. J. Org. Chem. 2000, 1547.
276. (c) Kratzer, B.; Mayer, T. G.; Schmidt, R. R. Tetrahedron Lett. 1993, 34, 6881.
277. (d) Mayer, T. G.; Kratzer, B.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2177.
278. (e) Mayer, T. G.; Schmidt, R. R. Liebigs Ann./Recueil 1997, 859.
279. (f) Leung, L. W.; Bittman, R. Carbohydr. Res. 1998, 305, 171.
280. See also: (g) Bittman, R.; Leung, L. W. U. S. Patent 5756774, 1998; Chem. Abstr. 1998, 129, 41368b.