Concise total syntheses of amphidinolides C and F

Chemistry - A European Journal

Volumn 21, Issue 6, 2015, Pages 2398-2408

  Valot, Gaëlle ^a   Mailhol, Damien ^a   Regens, Christopher S ^a   O'Malley, Daniel P ^a   Godineau, Edouard ^a   Takikawa, Hiroshi ^a   Philipps, Petra ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alkyne metathesis; Molybdenum; Natural products; Platinum; Total synthesis

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; CATALYSIS; CHAINS; CHEMICAL REACTIONS; CONDENSATION REACTIONS; DRUG PRODUCTS; ESTERIFICATION; ESTERS; HYDROCARBONS; KETONES; METABOLITES; MOLYBDENUM; PLATINUM; SUBSTRATES; SYNTHESIS (CHEMICAL);

ALKYNE METATHESIS; MARINE NATURAL PRODUCTS; NATURAL PRODUCTS; OXA-MICHAEL ADDITION; OXIDATIVE CYCLIZATION; STILLE CROSS-COUPLING; TOTAL SYNTHESIS; YAMAGUCHI ESTERIFICATIONS;

CYCLIZATION;

AMPHIDINOLIDE C; AMPHIDINOLIDE F; COBALT; CYCLOALKANE DERIVATIVE; MACROLIDE; PLATINUM;

CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COBALT; CYCLIZATION; CYCLOPARAFFINS; MACROLIDES; OXIDATION-REDUCTION; PLATINUM; STEREOISOMERISM;

EID: 84921745029     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201405790     Document Type: Article

References (186)

1. a) J. Kobayashi, T. Kubota, J. Nat. Prod. 2007, 70, 451-460;
2. b) J. Kobayashi,M. Tsuda, Nat. Prod. Rep. 2004, 21, 77-93.
3. a) J. Kobayashi, M. Ishibashi, M. R. Wälchli, H. Nakamura, Y. Hirata, T. Sasaki, Y. Ohizumi, J. Am. Chem. Soc. 1988, 110, 490-494;
4. b) T. Kubota, M. Tsuda, J. Kobayashi, Org. Lett. 2001, 3, 1363-1366;
5. c) T. Kubota, M.Tsuda, J. Kobayashi, Tetrahedron 2003, 59, 1613-1625.
6. T. Kubota, Y. Sakuma, M. Tsuda, J. Kobayashi, Mar. Drugs 2004, 2, 83-87.
7. T. Kubota, A. Suzuki, M. Yamada, S. Baba, J. Kobayashi, Heterocycles 2010, 82, 333-338.
8. J. Kobayashi, M. Tsuda, M. Ishibashi, H. Shigemori, T. Yamasu, H. Hirota, T. Sasaki, J. Antibiot. 1991, 44, 1259-1261.
9. Macrolide Antibiotics. Chemistry, Biology, and Practice (Ed.: S. O¯mura), 2nd ed., Academic Press, San Diego, 2002.
10. A. Fürstner, Isr. J. Chem. 2011, 51, 329-345.
11. a) H. Ishiyama, M. Ishibashi, J. Kobayashi, Chem. Pharm. Bull. 1996, 44, 1819-1822;
12. b) J. B. Shotwell, W. R. Roush, Org. Lett. 2004, 6, 3865-3868;
13. c) D. K. Mohapatra, H. Rahaman, M. S. Chorghade, M. K. Gurjar, Synlett 2007, 0567-0570;
14. d) R. H. Bates, J. B. Shotwell, W. R. Roush, Org. Lett. 2008, 10, 4343 -4346;
15. e) C. Palmer, N. A. Morra, A. C. Stevens, B. Bajtos, B. P. Machin, B. L. Pagenkopf, Org. Lett. 2009, 11, 5614-5617;
16. f) A. Armstrong, C. Pyrkotis, Tetrahedron Lett. 2009, 50, 3325-3328;
17. g) D. K. Mohapatra, P. Dasari, H. Rahaman, R. Pal, Tetrahedron Lett. 2009, 50, 6276-6279;
18. h) S. Mahapatra, R. G. Carter, Org. Biomol. Chem. 2009, 7, 4582-4585;
19. i) M. P. Paudyal, N. P. Rath, C. D. Spilling, Org. Lett. 2010, 12, 2954-2957;
20. j) L. Ferrié, B. Figadére, Org. Lett. 2010, 12, 4976-4979;
21. k) S. Roy, C. D. Spilling, Org. Lett. 2010, 12, 5326-5329;
22. l) N. A. Morra, B. L. Pagenkopf, Eur. J. Org. Chem. 2013, 756-760;
23. m) J. S. Clark, G. Yang, A. P. Osnowski, Org. Lett. 2013, 15, 1460-1463;
24. n) J. S. Clark, G. Yang, A. P. Osnowski, Org. Lett. 2013, 15, 1464-1467;
25. o) N. A. Morra, B. L. Pagenkopf, Tetrahedron 2013, 69, 8632-8644;
26. p) D. Wu, C. J. Forsyth, Org. Lett. 2013, 15, 1178-1181.
27. a) S. Mahapatra, R. G. Carter, J. Am. Chem. Soc. 2013, 135, 10792-10803;
28. b) S. Mahapatra, R. G. Carter, Angew. Chem. Int. Ed. 2012, 51, 7948-7951;
29. Angew. Chem. 2012, 124, 8072-8075.
30. G. Valot, C. S. Regens, D. P. O'Malley, E. Godineau, H. Takikawa, A. Fürstner, Angew. Chem. Int. Ed. 2013, 52, 9534-9538;
31. Angew. Chem. 2013, 125, 9713-9717.
32. a) A. Fürstner, C. Aïssa, R. Riveiros, J. Ragot, Angew. Chem. Int. Ed. 2002, 41, 4763-4766;
33. Angew. Chem. 2002, 114, 4958-4960;
34. b) C. Aïssa, R. Riveiros, J. Ragot, A. Fürstner, J. Am. Chem. Soc. 2003, 125, 15512-15520;
35. c) O. Lepage, E. Kattnig, A. Fürstner, J. Am. C hem. Soc. 2004, 126, 15970-15971;
36. d) A. Fürstner, E. Kattnig, O. Lepage, J. Am. Chem. Soc. 2006, 128, 9194-9204;
37. e) A. Fürstner, O. Larionov, S. Flügge, Angew. Chem. Int. Ed. 2007, 46, 5545-5548;
38. Angew. Chem. 2007, 119, 5641-5644.
39. a) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403;
40. b) E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350;
41. c) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211.
42. a) A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
43. Angew. Chem. 2007, 119, 3478-519;
44. b) A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208-3221.
45. A. Fürstner, Acc. Chem. Res. 2014, 47, 925-938.
46. Y. Zhang, T. Luo, Z. Yang, Nat. Prod. Rep. 2014, 31, 489-503.
47. a) A. Fürstner, H. Szillat, B. Gabor, R. Mynott, J. Am. Chem. Soc. 1998, 120, 8305-8314;
48. b) V. Mamane, P. Hannen, A. Fürstner, Chem. Eur. J. 2004, 10, 4556-4575;
49. c) A. Fürstner, P. Hannen, Chem. Eur. J. 2006, 12, 3006-3019;
50. d) A. Fürstner, A. Schlecker, Chem. Eur. J. 2008, 14, 9181-9191.
51. a) W. Chaladaj, M. Corbet, A. Fürstner, Angew. Chem. Int. Ed. 2012, 51, 6929-6933;
52. Angew. Chem. 2012, 124, 7035-7039;
53. b) S. Benson, M.-P. Collin, A. Arlt, B. Gabor, R. Goddard, A. Fürstner, Angew. Chem. Int. Ed. 2011, 50, 8739-8744;
54. Angew. Chem. 2011, 123, 8898-8903;
55. c) L. Hoffmeister, P. Persich, A. Fürstner, Chem. Eur. J. 2014, 20, 4396-4402;
56. d) L. Brewitz, J. Llaveria, A. Yada, A. Fürstner, Chem. Eur. J. 2013, 19, 4532-4537.
57. M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2011, 47, 6536-6544.
58. H. H. Jung, P. E. Floreancig, Org. Lett. 2006, 8, 1949-1951.
59. a) A. Fürstner, G. Seidel, Angew. Chem. Int. Ed. 1998, 37, 1734-1736;
60. Angew. Chem. 1998, 110, 1758-1760;
61. b) A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113.
62. a) A. Fürstner, Angew. Chem. Int. Ed. 2013, 52, 2794-2819;
63. Angew. Chem. 2013, 125, 2860-2887;
64. b) A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307-2320.
65. a) K. Lehr, R. Mariz, L. Leseurre, B. Gabor, A. Fürstner, Angew. Chem. Int. Ed. 2011, 50, 11373-11377;
66. Angew. Chem. 2011, 123, 11575-11579;
67. b) V. Hickmann, A. Kondoh, B. Gabor, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471-13480;
68. c) A. Guy, C. Oger, J. Heppekausen, C. Signorini, C. De Felice, A. Fürstner, T. Durand, J.-M. Galano, Chem. Eur. J. 2014, 20, 6374-6380;
69. J.-M. Galano, Chem. Eur. J. 2014, 20, 6374-6380.
70. a) A. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11799-11805;
71. b) A. Fürstner, T. Dierkes, Org. Lett. 2000, 2, 2463-2465;
72. c) A. Fürstner, C. Mathes, K. Grela, Chem. Commun. 2001, 1057-1059.
73. a) A. Fürstner, E. Kattnig, G. Kelter, H.-H. Fiebig, Chem. Eur. J. 2009, 15, 4030-4043;
74. b) A. Fürstner, S. Flügge, O. Larionov, Y. Takahashi, T. Kubota, J. Kobayashi, Chem. Eur. J. 2009, 15, 4011-4029.
75. a) A. Fürstner, L. Turet, Angew. Chem. Int. Ed. 2005, 44, 3462-3466;
76. Angew. Chem. 2005, 117, 3528-3532;
77. b) A. Fürstner, D. De Souza, L. Turet, M. D. B. Fenster, L. Parra-Rapado, C. Wirtz, R. Mynott, C. W. Lehmann, Chem. Eur. J. 2007, 13, 115-134.
78. a) J. Willwacher, A. Fürstner, Angew. Chem. Int. Ed. 2014, 53, 4217-4221;
79. Angew. Chem. 2014, 126, 4301-4305;
80. b) K. Micoine, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 14064-14066;
81. c) K. Micoine, P. Persich, J. Llaveria, M.-H. Lam, A. Maderna, F. Loganzo, A. Fürstner, Chem. Eur. J. 2013, 19, 7370-7383.
82. a) J. Heppekausen, R. Stade, A. Kondoh, G. Seidel, R. Goddard, A. Fürstner, Chem. Eur. J. 2012, 18, 10281-10299;
83. b) J. Heppekausen, R. Stade, R. Goddard, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11045-11057.
84. a) A. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453-9454;
85. b) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317;
86. c) A. Fürstner, K. Radkowski, J. Grabowski, C. Wirtz, R. Mynott, J. Org. Chem. 2000, 65, 8758-8762.
87. a) J. H. Wengrovius, J. Sancho, R. R. Schrock, J. Am. Chem. Soc. 1981, 103, 3932-3934;
88. b) M. L. Listemann, R. R. Schrock, Organometallics 1985, 4, 74-83.
89. a) S. Beer, K. Brandhorst, C. G. Hrib, X. Wu, B. Haberlag, J. Grunenberg, P. G. Jones, M. Tamm, Organometallics 2009, 28, 1534-1545;
90. b) S. Beer, C. G. Hrib, P. G. Jones, K. Brandhorst, J. Grunenberg, M. Tamm, Angew. Chem. Int. Ed. 2007, 46, 8890-8894;
91. Angew. Chem. 2007, 119, 9047-9051.
92. G. Jalce, X. Franck, B. Seon-Meniel, R. Hocquemiller, B. Figadère, Tetrahedron Lett. 2006, 47, 5905-5908.
93. A. Arcadi, S. Cacchi, F. Marinelli, Tetrahedron 1993, 49, 4955-4964.
94. B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907-4910.
95. a) M. Nishizawa, T. Takemoto, I. Sasaki, M. Nakano, E. Ho, K. Namba, H. Yamamoto, H. Imagawa, Synlett 2009, 1175-1179;
96. b) K. Ravindar, M. S. Reddy, P. Deslongchamps, Org. Lett. 2011, 13, 3178-3181;
97. c) G. Stork, R. Borch, J. Am. Chem. Soc. 1964, 86, 935-936.
98. a) P. W. Jennings, J. W. Hartman, W. C. Hiscox, Inorg. Chim. Acta 1994, 222, 317-322;
99. b) J. W. Hartman, L. Sperry, Tetrahedron Lett. 2004, 45, 3787-3788;
100. c) L. W. Francisco, D. A. Moreno, J. D. Atwood, Organometallics 2001, 20, 4237-4245.
101. a) K. Imi, K. Imai, K. Utimoto, Tetrahedron Lett. 1987, 28, 3127-3130;
102. b) K. Utimoto, Pure Appl. Chem. 1983, 55, 1845-1852.
103. a) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. Int. Ed. 2002, 41, 4563-4565;
104. Angew. Chem. 2002, 114, 4745-4747;
105. b) Y. Fukuda, K. Utimoto, J. Org. Chem. 1991, 56, 3729-3731;
106. c) Y. Fukuda, K. Utimoto, Bull. Chem. Soc. Jpn. 1991, 64, 2013-2015;
107. d) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. Int. Ed. 1998, 37, 1415-1418;
108. Angew. Chem. 1998, 110, 1475-1478;
109. e) N. Marion, R. S. Ramn, S. P. Nolan, J. Am. Chem. Soc. 2009, 131, 448-449;
110. f) A. Leyva, A. Corma, J. Org. Chem. 2009, 74, 2067-2074.
111. Y.-C. Lin, C.-H. Lin, C.-Y. Chen, S.-S. Sun, B. Pal, Org. Biomol. Chem. 2011, 9, 4507-4517.
112. J. A. Marshall, J. Org. Chem. 2007, 72, 8153-8166.
113. a) P. Lucio Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562;
114. b) A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Synthesis 1996, 1153-1174.
115. a) J. A. Marshall, N. D. Adams, J. Org. Chem. 1999, 64, 5201-5204;
116. b) J. A. Marshall, P. Eidam, H. S. Eidam, J. Org. Chem. 2006, 71, 4840-4844.
117. a) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 696-697;
118. b) B. A. Johns, C. M. Grant, J. A. Marshall, Org. Synth. 2002, 79, 59-71.
119. a) S. D. Rychnovsky, D. J. Skalitzky, Tetrahedron Lett. 1990, 31, 945-948;
120. b) S. D. Rychnovsky, B. N. Rogers, T. I. Richardson, Acc. Chem. Res. 1998, 31, 9-17.
121. I. Fleming, T. W. Newton, F. Roessler, J. Chem. Soc. Perkin Trans. 1 1981, 2527-2532.
122. X. Cai, M. S. Chorghade, A. Fura, G. S. Grewal, K. A. Jauregui, H. A. Lounsbury, R. T. Scannell, C. G. Yeh, M. A. Young, S. Yu, L. Guo, R. M. Moriarty, R. Penmasta, M. S. Rao, R. K. Singhal, Z. Song, J. P. Staszewski, S. M. Tuladhar, S. Yang, Org. Process Res. Dev. 1998, 2, 73-76.
123. a) Y. K. Nishida, M. Konno, Y. Fukushima, H. Ohrui, H. Meguro, Agric. Biol. Chem. 1986, 50, 191-193;
124. b) Y. Shiro, K. Kato, M. Fujii, Y. Ida, H. Akita, Tetrahedron 2006, 62, 8687-8695.
125. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
126. J. Parikh, W. von E. Doering, J. Am. Chem. Soc. 1967, 89, 5505-5507.
127. a) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387;
128. b) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
129. T. R. Hoye, C. S. Jeffrey, F. Shao, Nat. Protoc. 2007, 2, 2451-2458.
130. A. Arlt, S. Benson, S. Schulthoff, B. Gabor, A. Fürstner, Chem. Eur. J. 2013, 19, 3596-3608.
131. V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595.
132. S. Inoki, T. Mukaiyama, Chem. Lett. 1990, 67-70.
133. B. Menéndez Pérez, D. Schuch, J. Hartung, Org. Biomol. Chem. 2008, 6, 3532-3541.
134. a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938;
135. b) J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5-26.
136. W. Oppolzer, R. N. Radinov, Tetrahedron Lett. 1991, 32, 5777-5780.
137. P. Charreau, M. Julia, J.-N. Verpeaux, J. Organomet. Chem. 1989, 379, 201-210.
138. a) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993;
139. b) A. Parenty, X. Moreau, J.-M. Campagne, Chem. Rev. 2006, 106, 911-939;
140. A. Parenty, X. Moreau, G. Niel, J. M. Campagne, Chem. Rev. 2013, 113, PR1-PR40.
141. a) J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
142. Angew. Chem. 1986, 98, 504-519;
143. b) V. Farina, V. Krishnamurty, W. J. Scott, Org. React. 1997, 50, 1-652.
144. A. Fürstner, J.-A. Funel, M. Tremblay, L. C. Bouchez, C. Nevado, M. Waser, J. Ackerstaff, C. C. Stimson, Chem. Commun. 2008, 2873-2875.
145. a) A. Fürstner, L. C. Bouchez, J.-A. Funel, V. Liepins, F.-H. Porée, R. Gilmour, F. Beaufils, D. Laurich, M. Tamiya, Angew. Chem. Int. Ed. 2007, 46, 9265-9270;
146. Angew. Chem. 2007, 119, 9425-9430;
147. b) A. Fürstner, L. C. Bouchez, L. Morency, J.-A. Funel, V. Liepins, F.-H. Porée, R. Gilmour, D. Laurich, F. Beaufils, M. Tamiya, Chem. Eur. J. 2009, 15, 3983-4010.
148. G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748-2749.
149. J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119, 12376-12377.
150. a) A. Fürstner, J. Ackerstaff, Chem. Commun. 2008, 2870-2872;
151. b) A. Larivée, J. B. Unger, M. Thomas, C. Wirtz, C. Dubost, S. Handa, A. Fürstner, Angew. Chem. Int. Ed. 2011, 50, 304-309;
152. Angew. Chem. 2011, 123, 318-323.
153. a) A. Francais, A. Leyva, G. Etxebarria-Jardi, S. V. Ley, Org. Lett. 2010, 12, 340-343;
154. b) R. S. Paley, K. E. Berry, J. M. Liu, T. T. Sanan, J. Org. Chem. 2009, 74, 1611-1620;
155. c) I. Paterson, S. B. J. Kan, L. J. Gibson, Org. Lett. 2010, 12, 3724-3727;
156. d) I. Paterson, L. J. Gibson, S. B. J. Kan, Org. Lett. 2010, 12, 5530- 5533;
157. e) I. Paterson, T. Paquet, S. M. Dalby, Org. Lett. 2011, 13, 4398-4401;
158. f) A. Franc¸ais, A. Leyva-Pérez, G. Etxebarria-Jardi, J. PeCa, S. V. Ley, Chem. Eur. J. 2011, 17, 329-343;
159. g) S. Müller, T. Mayer, F. Sasse, M. E. Maier, Org. Lett. 2011, 13, 3940-3943;
160. h) C. Rink, V. Navickas, M. E. Maier, Org. Lett. 2011, 13, 2334-2337;
161. i) R. S. Paley, M. C. Laupheimer, N. A. K. Erskine, P. R. Rablen, R. D. Pike, J. S. Jones, Org. Lett. 2011, 13, 58-61;
162. j) M. Domínguez, S. Ávarez, R. Ávarez, Á. R. de Lera, Tetrahedron 2012, 68, 1756-1761;
163. k) L. Otero, B. Vaz, R. Ávarez, Á. R. de Lera, Chem. Commun. 2013, 49, 5043-5045;
164. l) H. Renata, Q. Zhou, P. S. Baran, Science 2013, 339, 59-63;
165. m) I. Paterson, K. K.-H. Ng, S. Williams, D. C. Millican, S. M. Dalby, Angew. Chem. 2014, 126, 2730-2733;
166. Angew. Chem. Int. Ed. 2014, 53, 2692-2995.
167. a) J. Gagnepain, E. Moulin, A. FÜrstner, Chem. Eur. J. 2011, 17, 6964-6972;
168. b) J. Gagnepain, E. Moulin, C. Nevado, M. Waser, A. Maier, G.Kelter, H.-H. Fiebig, A. Fürstner, Chem. Eur. J. 2011, 17, 6973-6984.
169. D. Mailhol, J. Willwacher, N. Kausch-Busies, E. E. Rubitski, Z. Sobol, M.Schuler, M.-H. Lam, S. Musto, F. Loganzo, A. Maderna, A. Fürstner, J. Am.Chem. Soc. 2014, 136, 15719-15729.
170. R. R. Schrock, Chem. Rev. 2002, 102, 145-179.
171. K. Gebauer, A. Fürstner, Angew. Chem. 2014, 126, 6511-6514;
172. Angew. Chem. Int. Ed. 2014, 53, 6393-6396.
173. a) P. Persich, J. Llaveria, R. Lhermet, T. de Haro, R. Stade, A. Kondoh, A. Fürstner, Chem. Eur. J. 2013, 19, 13047-13058;
174. b) R. Lhermet, A. Fürstner, Chem. Eur. J. 2014, 20, 13188-13193.
175. K. Bannai, T. Toru, T. O¯ba, T. Tanaka, N. Okamura, K. Watanabe, A. Hazato, S. Kurozumi, Tetrahedron 1986, 42, 6735-6746.
176. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
177. Catalytic TPAP is used in combination with N-methyl-morpholine-Noxide which, upon oxygen-transfer, releases the parent tertiary amine and hence renders the medium basic.
178. Occasionally, traces of epimers were detected, which had to be removed by preparative HPLC, obviously at the expense of the isolated yield.
179. S. Hara, H. Dojo, S. Takinami, A. Suzuki, Tetrahedron Lett. 1983, 24, 731-734.
180. W. A. Nugent, Chem. Commun. 1999, 1369-1370;
181. b) Y. K. Chen, S.-J. Jeon, P. J. Walsh, W. A. Nugent, Org. Synth. 2005, 82, 87-92;
182. c) J. G. Kim, P. J. Walsh, Angew. Chem. Int. Ed. 2006, 45, 4175-4178;
183. Angew. Chem. 2006, 118, 4281-4284.
184. R. Noyori, Asymmetric Catalysis in Organic Synthesis Wiley, New York, 1994.
185. A. Fürstner, Angew. Chem. 2014, 126, 8728-8740;
186. Angew. Chem. Int. Ed. 2014, 53, 8587-8598.