Photochemical reactions applied to the synthesis of helicenes and helicene-like compounds

Journal of Photochemistry and Photobiology C: Photochemistry Reviews

Volumn 19, Issue 1, 2014, Pages 1-19

  Hoffmann, Norbert ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Aromatic compounds; Chirality; Helicenes; Heterocycles; Photocyclization; Vollhardt reaction

Indexed keywords

ASYMMETRIC SYNTHESIS; BENZOCYCLOBUTENE; CYCLOPENTADIENES; HELICENES; HETEROCYCLES; OPTICAL RESOLUTION; PHOTOCYCLIZATION; VOLLHARDT REACTION;

AROMATIC COMPOUNDS; CHIRALITY;

PHOTOCHEMICAL REACTIONS;

EID: 84890423211     PISSN: 13895567     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochemrev.2013.11.001     Document Type: Review

References (234)

1. Vögtle F. Reizvolle Moleküle der Organischen Chemie 1989, B.G. Teubner, Stuttgart.
2. Vögtle F. Fascinating Molecules in Organic Chemistry 1992, Wiley, New York.
3. Newman M.S., Lednicer D. J. Am. Chem. Soc. 1956, 78:4765.
4. Joly M., Defay N., Martin R.H., Declereq J.P., Germain G., Soubrier-Payen B., Van Meerssche M. Helv. Chim. Acta 1977, 60:537.
5. Fuchter M.J., Weimar M., Yang X., Judge D.K., White A.J.P. Tetrahedron Lett. 2012, 53:1108.
6. Mason S.F. Fundamental Aspects and Recent Developments in Optical Rotatory Dispersion and Circular Dichroism 1973, 27-40. Heyden & Son Ltd., London. F. Ciardelli, P. Salvadori (Eds.).
7. Weigan O.E. Fundamental Aspects and Recent Developments in Optical Rotatory Dispersion and Circular Dichroism 1973, 50-65. Heyden & Son Ltd., London. F. Ciardelli, P. Salvadori (Eds.).
8. Snatzke G., Kajtár M., Snatzke F. Fundamental Aspects and Recent Developments in Optical Rotatory Dispersion and Circular Dichroism 1973, 148-172. Heyden & Son Ltd., London. F. Ciardelli, P. Salvadori (Eds.).
9. Nakai Y., Mori T., Sato K., Inoue Y. J. Phys. Chem. A 2013, 117:5082.
10. Nakai Y., Mori T., Inoue Y. J. Phys. Chem. A 2013, 117:83.
11. Nakai Y., Mori T., Inoue Y. J. Phys. Chem. A 2012, 116:7372.
12. Elm J., Lykkebo J., Sørensen T.J., Laursen B.W., Mikkelsen K.V. J. Phys. Chem. A 2011, 115:12025.
13. Caronna T., Fontana F., Longhi G., Mele A., Sora I.N., Panzeri W., Viganò L. ARKIVOC 2009, (viii):145.
14. Botek E., Campagne B. J. Chem. Phys. 2007, 127:204101.
15. Rulíšek L., Exner O., Cwiklik L., Jungwirth P., Starý I., Pospíšil L., Havlas Z. J. Phys. Chem. C 2007, 111:14948.
16. Furche F., Ahlrichs A., Wachsmann C., Weber E., Sobanski A., Vögtle F., Grimme S. J. Am. Chem. Soc. 2000, 122:1717.
17. Bürgi T., Urakawa A., Behzadi B., Ernst K.-H., Baiker A. New J. Chem. 2004, 28:332.
18. Ohta E., Sato H., Ando S., Kosaka A., Fukushima T., Hashizume D., Yamasaki M., Hasegawa K., Muraoka A., Ushiyama H., Yamashita K., Aida T. Nat. Chem. 2011, 3:68.
19. Wynberg H. Acc. Chem. Res. 1971, 4:65.
20. Martin R.H. Angew. Chem. Int. Ed. 1974, 13:649.
21. Laarhoven W.H., Prinsen W.J.C. Top. Curr. Chem. 1984, 125:63.
22. Meurer K.P., Vögtle F. Top. Curr. Chem. 1985, 127:1.
23. Grimme S., Harren J., Sobanski A., Vögtle F. Eur. J. Org. Chem. 1998, 1491.
24. Shen Y., Chen C.-F. Chem. Rev. 2012, 112:1463.
25. Gingras M. Chem. Soc. Rev. 2013, 42:968.
26. Gingras M., Félix G., Peresutti R. Chem. Soc. Rev. 2013, 42:1007.
27. Gingras M. Chem. Soc. Rev. 2013, 42:1051.
28. Urbano A., Carreño M.C. Org. Biomol. Chem. 2013, 11:699.
29. Dumitrascu F., Dumitrescu D.G., Aron I. ARKIVOC 2010, (i):1.
30. Katz T.J. Angew. Chem. Int. Ed. 2000, 39:1991.
31. Urbano A. Angew. Chem. Int. Ed. 2003, 42:3986.
32. Stará I.G., Starý I. Science of Synthesis Science of Synthesis 2010, vol. 45b:885-953. Thieme, Stuttgart.
33. Hopf H. Classics in Hydrocarbon Chemistry 2000, Wiley-VCH, Weinheim.
34. Strained Hydrocarbons 2009, Wiley-VCH, Weinheim. H. Dodziuk (Ed.).
35. Hoffmann N. Chem. Rev. 2008, 108:1052.
36. Hehn J., Bach T. Angew. Chem. Int. Ed. 2011, 50:1000.
37. Hoffmann N. Photochem. Photobiol. Sci. 2012, 11:1613.
38. Coyle E.E., Oelgemöller M. Photochem. Photobiol. Sci. 2008, 7:1313.
39. Oelgemöller M., Shvydkiv O. Molecules 2011, 16:7522.
40. Fukuyama T., Rahman M.T., Sato M., Ryu I. Synlett 2008, 151.
41. Matsushita Y., Ichimura T., Ohba N., Kumada S., Sakeda K., Suzuki T., Tanibata H. Pure Appl. Chem. 2007, 79:1959.
42. Wegner J., Ceylan S., Kirschning A. Adv. Synth. Catal. 2012, 354:17.
43. Knowles J.P., Elliott L.D., Booker-Milburn K.I. Beilstein J. Org. Chem. 2012, 8:2025.
44. Wiles C., Watts P. Green Chem. 2012, 14:38.
45. Zimmerman H.E. Angew. Chem. Int. Ed. 1969, 8:1.
46. Turro N.J. Angew. Chem. Int. Ed. 1986, 25:882.
47. Olivucci M., Santoro F. Angew. Chem. Int. Ed. 2008, 47:6322.
48. Turro N.J., Ramamurthy V., Scaiano J.C. Modern Molecular Photochemistry of Organic Molecules 2010, University Science Books, Sausalito.
49. Klán P., Wirz J. Photochemistry of Organic Compounds 2009, Wiley, Chichester.
50. Terfort A., Görls H., Brunner H. Synthesis 1997, 79.
51. Reetz M.T., Beuttenmüller E.W., Goddard R. Tetrahedron Lett. 1997, 38:3211.
52. El Abed R., Aloui F., Genêt J.-P., Ben Hassine B., Marinetti A. J. Organomet. Chem. 2007, 692:1156.
53. Wachsmann C., Weber E., Czugler M., Seicher W. Eur. J. Org. Chem. 2003, 2863.
54. Ben Hassine B., Gorsane M., Gaerts-Evrard F., Pecher P., Martin R.H., Castelet D. Bull. Soc. Chim. Belg. 1986, 95:547.
55. Stammel C., Fröhlich R., Wolff C., Wenck H., de Meijere A., Mattay J. Eur. J. Org. Chem. 1999, 1709.
56. Görner H., Stammel C., Mattay J. J. Photochem. Photobiol. A: Chem. 1999, 120:171.
57. Takenaka N., Chen J., Captain B., Sarangthem R.S., Chandrakumar A. J. Am. Chem. Soc. 2010, 132:4536.
58. Crittall M.R., Rzepa H.S., Carbery D.R. Org. Lett. 2011, 13:1250.
59. Chen J., Captain B., Takenaka N. Org. Lett. 2012, 13:1654.
60. Sato I., Yamashima R., Kadowaki K., Yamamoto J., Shibata T., Soai K. Angew. Chem. Int. Ed. 2001, 40:1096.
61. Kawasaki T., Suzuki K., Licandro E., Bossi A., Maiorana S., Soai K. Tetrahedron: Asymmetry 2006, 17:2050.
62. Soai K., Kawasaki T. Chirality 2006, 18:469.
63. Soai K., Sato I., Shibata T. Chem. Rec. 2001, 1:321.
64. Soai K., Shibata T., Sato I. Acc. Chem. Res. 2000, 33:382.
65. Palmans A.R.A., Meijer E.W. Angew. Chem. Int. Ed. 2007, 46:8948.
66. Nakazaki M., Yamamoto K., Ikeda T., Kitsuki T., Okamoto Y. J. Chem. Soc. 1983, 785.
67. Pu L. Chem. Rev. 2004, 104:1687.
68. Amemiya R., Yamaguchi M. Org. Biomol. Chem. 2008, 6:26.
69. Ben Hassine B., Gosane M., Pecher J., Martin R.H. Bull. Chem. Soc. Belg. 1985, 94:597.
70. Ben Hassine B., Gosane M., Pecher J., Martin R.H. Bull. Chem. Soc. Belg. 1985, 94:759.
71. Ben Hassine B., Gosane M., Pecher J., Martin R.H. Bull. Chem. Soc. Belg. 1987, 96:801.
72. Bell T.W., Hext N.M. Chem. Soc. Rev. 2004, 33:589.
73. Zhang W., Moore J.S. Angew. Chem. Int. Ed. 2006, 45:4415.
74. Pieraccini S., Ferrarini A., Spada G.P. Chirality 2008, 20:749.
75. Sahasithiwat S., Mophuang T., Menbangpung L., Kamtonwong S., Sooksimuang T. Synth. Met. 2010, 160:1148.
76. Xu Y., Zhang Y.X., Sugiyama H., Umano T., Osuga H., Tanaka K. J. Am. Chem. Soc. 2004, 126:6566.
77. Honzawa S., Okubo H., Anzai S., Yamaguchi M., Tsumoto K., Kumagai I. Bioorg. Med. Chem. 2002, 10:3213.
78. Shinohara K., Sannohe Y., Kaieda S., Tanaka K., Osuga H., Tahara H., Xu Y., Kawase T., Bando T., Sugiyama H. J. Am. Chem. Soc. 2010, 132:3778.
79. Basili S., Basso G., Faccio A., Granzhan A., Ihmels H., Moro S., Viola G. ChemMedChem 2008, 3:1671.
80. Mallory F.B., Mallory C.W. Org. React. 1984, 30:1.
81. Mazzucato U., Momicchioli F. Chem. Rev. 1991, 91:1679.
82. Arai T., Tokumaru K. Chem. Rev. 1993, 93:23.
83. Laarhoven W.H. Org. Photochem. 1989, 10:163.
84. Jørgensen K.B. Molecules 2010, 15:4334.
85. Saltiel J., Sears D.F., Ko D.-H., Park K.-M. CRC Handbook of Organic Photochemistry and Photobiology 1995, 3-49. CRC Press, Boca Raton. W.M. Horspool, P.-S. Song (Eds.).
86. Gilbert A. CRC Handbook of Organic Photochemistry and Photobiology 2004, 33/1-33/33. CRC Press, Boca Raton. second ed. W. Horspool, F. Lenci (Eds.).
87. Hoffmann N. CRC Handbook of Organic Photochemistry and Photobiology 2004, 34/1-34/34. CRC Press, Boca Raton. second ed. W. Horspool, F. Lenci (Eds.).
88. Flamang-Barbieux M., Nasielski J., Matin R.H. Tetrahedron Lett. 1967, 8:743.
89. Laarhoven W.H., Cuppen Th.J.H.M., Nivard R.J.F. Tetrahedron 1970, 26:4865.
90. Woodward R.B., Hoffmann R. Angew. Chem. Int. Ed. 1969, 8:781.
91. Scholz M., Mühlstädt M., Dietz F. Tetrahedron Lett. 1967, 8:665.
92. Dietz F., Scholz M. Tetrahedron 1968, 24:6845.
93. Laarhoven W.H., Cuppen Th.J.H.M., Nivard R.J.F. Recl. Trav. Chim. Pays-Bas 1968, 87:687.
94. Martin R.H., Flammang-Barbieux M., Cosyn J.P., Gelbeke M. Tetrahedron Lett. 1968, 9:3507.
95. Martin R.H., Baes M. Tetrahedron 1975, 31:2135.
96. Sudhakar A., Katz T.J. Tetrahedron Lett. 1986, 27:2231.
97. Martin R.H., Eyndels C., Defay N. Tetrahedron Lett. 1972, 13:2731.
98. Wilcox C.F., Lahti P.M., Rocca J.R., Halpern M.B., Meinwald J. Tetrahedron Lett. 1978, 19:1893.
99. Liu L., Katz T.J. Tetrahedron Lett. 1991, 32:6831.
100. Gingras M., Collet C. Synlett 2007, 2337.
101. Martin R.H., Marchant M.-J., Baes M. Helv. Chim. Acta 1971, 54:358.
102. Liu L., Yang B., Katz T.J., Poindexter M.K. J. Org. Chem. 1991, 56:3769.
103. Sudhakar A., Katz T.J. J. Am. Chem. Soc. 1986, 108:179.
104. Reetz M.T., Sostmann S. Tetrahedron 2001, 57:2515.
105. Hernandez-Perez A.C., Vlassova A., Collins S.K. Org. Lett. 2012, 14:2988.
106. McMillin D.R., McNett K.M. Chem. Rev. 1998, 98:1201.
107. Horváth O. Coord. Chem. Rev. 1994, 135/136:303.
108. Dey D., Basu S. J. Lumin. 2011, 131:732.
109. Prier C.K., Rankic D.A., MacMillan D.W.C. Chem. Rev. 2013, 113:5322.
110. Xi Y., Yi H., Lei A. Org. Biomol. Chem. 2013, 11:2387.
111. Shi L., Xia W. Chem. Soc. Rev. 2012, 41:7687.
112. Yoon T.P., Ischay M.A. Nat. Chem. 2010, 2:527.
113. Narayanam J.M.R., Stephenson C.R.J. Chem. Soc. Rev. 2011, 40:102.
114. Zeidler K. Angew. Chem. Int. Ed. 2009, 48:9785.
115. Fields E.K., Behrend S.J., Meyerson S., Winzenburg M.L., Ortega B.R., Hall H.K. J. Org. Chem. 1990, 55:5165.
116. Firmer A.A., Kinder J.D., Youngs W.J., Meador M.A.B. J. Org. Chem. 1995, 60:1658.
117. Sato K., Yamagishi T., Arai S. J. Heterocycl. Chem. 2000, 37:1009. For an example of heterohelicene synthesis see:.
118. E.K. Fields, M.L. Winzenburg, S.J. Behrend (Standard Oil Company), US 4,569,867 (1986).
119. E.K. Fields, M.L. Winzenburg, S.J. Behrend (Standard Oil Company), US 4,638,072 (1987).
120. Pathak R., Vandayar K., van Otterlo W.A.L., Michael J.P., Fernandes M.A., de Koning C.B. Org. Biomol. Chem. 2004, 2:3504.
121. Hu J.-Y., Paudel A., Sato N., Feng X., Era M., Matsumoto T., Tanaka J., Elsegood M.R.J., Redshaw C., Yamato T. Org. Biomol. Chem. 2013, 11:2186.
122. Paudel A., Hu J.-Y., Yamato T. J. Chem. Res. 2008, 457.
123. Vollhardt K.P.C. Angew. Chem. Int. Ed. Engl. 1984, 23:539.
124. Gandon V., Aubert C., Malacria M. Chem. Commun. 2006, 2209.
125. Chopade P.R., Louie J. Adv. Synth. Catal. 2006, 348:2307.
126. Hess W., Treutwein J., Hilt G. Synthesis 2008, 3537.
127. Scheuermann née Taylor C.J., Ward B.D. New J. Chem. 2008, 32:1850.
128. Tanaka K. Chem. Asian J. 2009, 4:508.
129. Rajca A., Rajca S. Angew. Chem. Int. Ed. 2010, 49:672.
130. Dominguez G., Pérez-Castells J. Chem. Soc. Rev. 2011, 40:3430.
131. Saito S., Yamamoto Y. Chem. Rev. 2000, 100:2901.
132. Hoffmann N. ChemSusChem 2012, 5:352.
133. Teplý F. Collect. Czech. Chem. Commun. 2011, 76:859.
134. Teplý F., Stará I.G., Starý I., Kollárovič A., Šaman D., Vyskočil S., Fiedler P. J. Org. Chem. 2003, 68:5193.
135. Balaban A.T., Vollhardt K.P.C. Open Org. Chem. J. 2011, 5:117.
136. Schmidt-Radde R.H., Vollhardt K.P.C. J. Am. Chem. Soc. 1992, 114:9713.
137. Han S., Bond A.D., Disch R.L., Holmes D., Schulman J.M., Teat S.T., Vollhardt K.P.C., Whitener G.D. Angew. Chem. Int. Ed. 2002, 41:3223.
138. Han S., Anderson D.R., Bond A.D., Chu H.V., Disch R.L., Holmes D., Schulman J.M., Teat S.T., Vollhardt K.P.C., Whitener G.D. Angew. Chem. Int. Ed. 2002, 41:3227.
139. Collins S.K., Vachon M.P. Org. Biomol. Chem. 2006, 4:2518.
140. Tanaka K. Nonlin. Opt. 1999, 22:329.
141. Rajca A., Miyasaka M. Functional Organic Materials. Strategies, and Applications 2007, 547-581. Wieley-VCH, Weinheim. T.J.J. Müller, U.H.F. Bunz (Eds.).
142. Rajca A., Rajca S., Pink M., Miyasaka M. Synlett 2007, 1799.
143. Abate S., Bazzini C., Caronna T., Fontana F., Gambarotti C., Gangemi F., Longhi G., Mele A., Sora I.N., Pazeri W. Tetrahedron 2006, 62:139.
144. Bazzini C., Brovelli S., Caronna T., Gambarotti C., Giannone M., Macchi P., Meinardi F., Mele A., Panzeri W., Recupero F., Sironi A., Tubino R. Eur. J. Org. Chem. 2005, 1247.
145. Aloui F., El Abed R., Ben Hassine B. Tetrahedron Lett. 2008, 49:1455.
146. Arai S., Nakamura N., Yamaguchi H., Okazaki M., Hida M. Bull. Chem. Soc. Jpn. 1991, 64:1996.
147. Sato K., Nakajima K., Arai S., Yamagishi T. Liebigs Ann. 1966, 439.
148. Arai S., Ishikura M., Yamagishi T. J. Chem. Soc. Perkin Trans. 1998, 1:1561.
149. Arai S., Takeuchi T., Ishikawa M., Takeuchi T., Yamazaki M., Hida M. J. Chem. Soc. Perkin Trans. 1987, 1:481.
150. Arai S., Yafune T., Okubo M., Hida M. Tetrahedron Lett. 1989, 30:7217.
151. Arai S., Nakamura N., Yamagushi H., Okazaki M., Hida M. Bull. Chem. Soc. Jpn. 1991, 64:1996.
152. Sato K., Yamagishi T., Arai S. J. Heterocycl. Chem. 2000, 37:1009.
153. Lenz G.R. Synthesis 1978, 487.
154. Kaupp G. Angew. Chem. Int. Ed. 1980, 19:243.
155. Grimshaw J., de Silva A.P. Chem. Soc. Rev. 1981, 10:181.
156. Ninomiya I., Naito T. Photochemical Synthesis 1989, Academic Press, London.
157. Kessar S.V., Mankotia A.K.S. CRC Handbook of Organic Photochemistry and Photobiology 1995, 1218-1228. CRC Press, Boca Raton. W.M. Horspool, P.-S. Song (Eds.).
158. Luo J.-K., Ferderspiel R.F., Castle R.N. J. Heterocycl. Chem. 1992, 29:963.
159. Dopper J.H., Oudman D., Wynberg H. J. Am. Chem. Soc. 1973, 95:3692.
160. Groen M.B., Schadenberg H., Wynberg H. J. Org. Chem. 1971, 36:2797.
161. Yamada K., Ogahiwa S., Tanaka H., Nakagawa H., Kawazura H. Chem. Lett. 1981, 343.
162. Maiorana S., Papagni A., Licandro E., Annunziata R., Paravidino P., Perdicchia D., Giannini C., Benicini M., Clays K., Persoons A. Tetrahedron 2003, 59:6481.
163. Caronna F., Catellani M., Luzzati S., Malpezzi L., Meille S.V., Mele A., Richter C., Sinisi R. Chem. Mater. 2001, 13:3906.
164. Wynberg H., Groen M.B. J. Am. Chem. Soc. 1970, 92:6664.
165. Lehman P.G., Wynberg H. Aust. J. Chem. 1974, 27:315.
166. Waghray D., Nulens W., Dehaen W. Org. Lett. 2011, 13:5516.
167. Liu X., Yu P., Xu L., Yang J., Shi J., Wang Z., Cheng Y., Wang H. J. Org. Chem. 2013, 78:6316.
168. Míšek J., Teplý F., Stará I.G., Tichý M., Šaman D., Císařová I., Vojtíšek P., Starý I. Angew. Chem. Int. Ed. 2008, 47:3188.
169. Sato K., Okazaki S., Arai S. J. Heterocycl. Chem. 2004, 41:443.
170. Shi L., Liu Z., Dong G., Duan L., Qiu Y., Jia J., Guo W., Zhao D., Cui D., Tao X. Chem. Eur. J. 2012, 18:8092.
171. Caronna T., Gabbiadini S., Mele A., Recupero F. Helv. Chim. Acta 2002, 85:1.
172. Waghray D., Zhang J., Jacobs J., Nulens W., Basaric N., Van Meervelt L., Dehaen W. J. Org. Chem. 2012, 77:10176.
173. Thompson C.M., Docter S. Tetrahedron Lett. 1988, 29:5213.
174. Yavari K., Moussa S., Ben Hassin B., Retailleau P., Voituriez A., Marinetti A. Angew. Chem. Int. Ed. 2012, 51:6748.
175. Yavari K., Retailleau P., Voituriez A., Marinetti A. Chem. Eur. J. 2013, 19:9939.
176. Graule S., Rudolph M., Vanthuyne N., Autschbach J., Roussel C., Crassous F., Réau R. J. Am. Chem. Soc. 2009, 131:3183.
177. Norsten T.B., Peters A., McDonald A., Wang M., Branda N.R. J. Am. Chem. Soc. 2001, 123:7447.
178. Irie M. Chem. Rev. 2000, 100:1685.
179. Wigglesworth T.J., Sud D., Norsten T.B., Lekhi V.S., Branda N.R. J. Am. Chem. Soc. 2005, 127:7272.
180. Okuyama T., Tani Y., Miyake K., Yokoyama Y. J. Org. Chem. 2007, 72:1634.
181. Stará I.G., Starý I., Kollárovič A., Teplý F., Šaman D., Tichý M. J. Org. Chem. 1998, 63:4046.
182. Alabugin I.V., Gilmore K.M., Peterson P.W. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011, 1:109.
183. Dilthey W., Quint F. Ber. Dtsch. Chem. Ges. 1936, 69:1575.
184. Dilthey W., Quint F., Heinen J. J. Prakt. Chem. 1939, 152:49.
185. Dilthey W., Quint F., Stephan J.H. J. Prakt. Chem. 1939, 152:99.
186. Rau H. Chem. Rev. 1983, 83:535.
187. Inoue Y. Chem. Rev. 1992, 92:741.
188. Chiral Photochemistry 2004, Marcel Dekker, New York. Y. Inoue, V. Ramamurthy (Eds.).
189. Griesbeck A.G., Meierhenrich U.J. Angew. Chem. Int. Ed. 2002, 41:3147.
190. Collet A., Crassous J., Dutasta J.-P., Guy L. Molécules chirales 2009, EDP Sciences et CNRS Editions.
191. Feringa B.L., van Delden R.A. Angew. Chem. Int. Ed. 1999, 38:3418.
192. Mislow K. Collect. Czech. Chem. Commun. 2003, 69:849.
193. Kagan H.B., Balavoine G., Moradpour A. J. Mol. Evol. 1974, 4:41.
194. Nicoud J.-F. Actual. Chim. 2004, 279:15.
195. Buchhardt O. Angew. Chem. Int. Ed. 1974, 13:179.
196. Moradpour A., Nicoud J.F., Balavoine G., Kagan H., Tsoucaris G. J. Am. Chem. Soc. 1971, 93:2353.
197. Kagan H., Moradpour A., Nicoud J.F., Balavoine G., Martin R.H., Cosy J.P. Tetrahedron Lett. 1971, 12:2479.
198. Tsoucaris G., Balavoine G., Morapour A., Nicoud J.-F., Kagan H. C. R. Acad. Sci. Ser. B 1971, 272:1271.
199. Bernstein W.J., Calvin M., Buchardt O. Tetrahedron Lett. 1972, 13:2195.
200. Bernstein W.J., Calvin M., Buchardt O. J. Am. Chem. Soc. 1972, 94:494.
201. Martin R.H., Marchant M.J. Tetrahedron 1974, 30:343.
202. Bernstein W.J., Calvin M., Burchardt O. J. Am. Chem. Soc. 1973, 95:527.
203. Moradpour A., Kagan H., Baes M., Morren G., Martin R.H. Tetrahedron 1975, 31:2139.
204. Balavoine B., Moradpour A., Kagan H.B. J. Am. Chem. Soc. 1974, 96:5152.
205. Nakazaki M., Yamamoto K., Fujiwara K. Chem. Lett. 1978, 863.
206. Hibert M., Solladie G. J. Org. Chem. 1980, 45:5393.
207. Prinsen W.J.C., Laarhoven W.H. Recl. Trav. Chim. Pays-Bas 1995, 114:470.
208. Lin Y., Chien L.-C. Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A 1997, 301:267.
209. Heller B., Hapke M., Fischer C., Andronova A., Stary I., Stara I.G. J. Organomet. Chem. 2013, 723:98.
210. Gutnov A., Heller B., Fischer C., Drexler H.-J., Spannenberg A., Sundermann B., Sundermann C. Angew. Chem. Int. Ed. 2004, 43:3795.
211. Pearson M.S.M., Carbery D.R. J. Org. Chem. 2009, 74:5320.
212. Vanest J.M., Martin R.H. Recl. Trav. Chim. Pays-Bas 1979, 98:113.
213. Tanaka K., Osuga H., Shogase Y., Suzuki H. Tetrahedron Lett. 1995, 36:915.
214. Osuga H., Suzuki H., Tanaka K. Bull. Chem. Soc. Jpn. 1997, 70:897.
215. El Abed R., Ben Hassine B., Genêt J.-P., Gorsane M., Madec J., Ricard L., Marinetti A. Synthesis 2004, 2513.
216. Katz T.J., Sudhakar A., Teasley M.F., Gilbert A.M., Geiger W.E., Robben M.P., Wuensch M., Ward M.D. J. Am. Chem. Soc. 1993, 115:3182.
217. Katz T.J., Pesti J. J. Am. Chem. Soc. 1982, 104:346.
218. Tribout J., Martin R.H., Doyle M., Wynberg H. Tetrahedron Lett. 1972, 13:2839.
219. Martin R.H., Libert V. J. Chem. Res. S 1980, 130.
220. Žádný J., Jančařík A., Andronova A., Šámal M., Vacek Chocholoušová J., Vacek J., Pohl R., Šaman D., Císařová I., Stará I.G., Starý I. Angew. Chem. Int. Ed. 2012, 51:5857.
221. Sehnal P., Stará I.G., Šaman D., Tichý M., Míšek J., Cvačka J., Rulíšek L., Chocholoušová J., Vacek J., Goryl G., Szymonski M., Císařová I., Starý I. Proc. Natl. Acad. Sci. U. S. A. 2009, 106:13169.
222. Sehnal P., Krausová Z., Teplý F., Stará I.G., Starý I., Rulíšek L., Šaman D., Císařová I. J. Org. Chem. 2008, 73:2074.
223. Stará I.G., Alexandrová Z., Teplý F., Sehnal P., Starý I., Šaman D., Buděšínský M., Cvačka J. Org. Lett. 2005, 7:2547.
224. Songis O., Míšek J., Schmidt M.B., Kollárovič A., Stará I.G., Šaman D., Císařová I., Starý I. J. Org. Chem. 2010, 75:6889.
225. Jacques J., Collet A., Wilen S.H. Enantiomers, Racemates, and Resolutions 1981, Krieger Publishing Company, Malabar.
226. Wynberg H., Groen M.B. J. Am. Chem. Soc. 1968, 90:5339.
227. Newman M.S., Lutz W.B., Lednicer D. J. Am. Chem. Soc. 1956, 77:3420.
228. Lightner D.A., Hefelfinger D.T., Powers T.W., Frank G.W., Trueblood K.N. J. Am. Chem. Soc. 1972, 94:3492.
229. Nakagawa H., Yamada K., Kawazura H. J. Chem. Soc. Chem. Commun. 1989, 1378.
230. Yamaguchi M., Okubo H., Hirama M. Chem. Commun. 1996, 1771.
231. Bell F., Waring D.H. J. Chem. Soc. 1949, 2689.
232. Wang D.Z., Katz T.J. J. Org. Chem. 2005, 70:8497.
233. Tanaka K., Shogase Y., Osuga H., Suzuki H., Nakamura K. Tetrahedron Lett. 1995, 36:1675.
234. Tanaka K., Osuga H., Suzuki H., Shogase Y., Kitahara Y. J. Chem. Soc. Perkin Trans. 1998, 1:935.