Multi-bond forming processes in efficient synthesis

Australian Journal of Chemistry

Volumn 66, Issue 3, 2013, Pages 267-283

  Green, Nicholas J ^a   Sherburn, Michael S ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CUTTING EDGES; EFFICIENT SYNTHESIS; STRUCTURAL COMPLEXITY; SYNTHETIC ORGANIC CHEMISTRY;

CHEMISTRY;

EID: 84875460273     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH13003     Document Type: Conference Paper

References (289)

1. The official website of the Nobel Prize, nobelprize.org, lists 2010 Nobel Prize to Heck, Negishi, and Suzuki "for palladiumcatalysed cross couplings in organic synthesis".
2. Nobel Prize to Chauvin, Grubbs, and Schrock "for the development of the metathesis method in organic synthesis".
3. K. C. Nicolaou, J. S. Chen, Classics in Total Synthesis III 2011 (Wiley-VCH: Weinheim).
4. M. Razzak, J. K. De Brabander, Nat. Chem. Biol. 2011, 7, 865. doi:10.1038/NCHEMBIO.709
5. We are referring to limits imposed by the laws of nature here.
6. The ideal synthesis is an idea initially articulated by Hendrickson and then developed and championed by Wender. See: J. B. Hendrickson, J. Am. Chem. Soc. 1975, 97, 5784. doi:10.1021/JA00853A023
7. P. A. Wender, M. P. Croatt, B. Witulski, Tetrahedron 2006, 62, 7505. doi:10.1016/J.TET.2006.02.085
8. P. A. Wender, B. L. Miller, Nature 2009, 460, 197. doi:10.1038/460197A
9. See also: T. Gaich, P. S. Baran, J. Org. Chem. 2010, 75, 4657. doi:10.1021/JO1006812
10. We do not wish to underplay the importance of total synthesis. There is pressing need for total synthesis to continue to pioneer new methods and strategies as stepping stones towards the 'ideal synthesis'. For a discussion of the problem of total synthesis within the context of a specific natural product/medicinal agent, see: A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477.
11. H. Ledford, Nature 2010, 468, 608. doi:10.1038/468608A
12. We eschew the word 'multiple' in favour of 'multi', in order to prevent any possible association with unsaturated bonds.
13. L. F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl. 1993, 32, 131. doi:10.1002/ANIE.199301313
14. L. Albrecht, H. Jiang, K. A. Jorgensen, Angew. Chem. Int. Ed. 2011, 50, 8492. doi:10.1002/ANIE.201102522
15. L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, 1st ed., 2006 (Wiley-VCH: Weinheim).
16. R. Robinson, J. Chem. Soc. Trans. 1917, 111, 762. doi:10.1039/ CT9171100762
17. J. Chiefari, Y. K. Chong, F. Ercole, J. Krstina, J. Jeffery, T. P. T. Le, R. T. A. Mayadunne, G. F. Meijs, C. L. Moad, G. Moad, E. Rizzardo, S. H. Thang, Macromolecules 1998, 31, 5559. doi:10.1021/MA9804951
18. W. S. Johnson, M. B. Gravestock, B. E. McCarry, J. Am. Chem. Soc. 1971, 93, 4332. doi:10.1021/JA00746A062
19. A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552. doi:10.1021/JA026216D
20. Controlled and Living Polymerizations: From Mechanisms to Applications, (Eds. K. Matyjaszewski, A. H. E.Muller) 2009 (Wiley-VCH: Weinheim).
21. For reviews on polymerisation, see: G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2012, 65, 985. doi:10.1071/CH12295
22. Synthesis of Polymers (Eds. D. A. Schluter, C. Hawker, J. Sakamoto) 2012 (Wiley-VCH: Weinheim).
23. Z. Wang, L. Zhou, K. El-Boubbou, X.-S. Ye, X. Huang, J. Org. Chem. 2007, 72, 6409. doi:10.1021/JO070585G
24. O. J. Plante, E. R. Palmacci, P. H. Seeberger, Science 2001, 291, 1523. doi:10.1126/SCIENCE.1057324
25. W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T.-T. Li, D. J. Faulkner, M. R. Petersen, J. Am. Chem. Soc. 1970, 92
26. doi:10.1021/JA00706A074
27. W. R. Roush, R. J. Sciotti, J. Am. Chem. Soc. 1998, 120, 7411. doi:10.1021/JA980611F
28. O. Diels, K. Alder, Justus Liebigs Ann. Chem. 1928, 460, 98. doi:10.1002/JLAC.19284600106
29. I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc., Perkin Trans. 1 1973, 977. doi:10.1039/P19730000977
30. With the occasional exception involving consecutive reactions, as noted.
31. G. Stork, A. W. Burgstahler, J. Am. Chem. Soc. 1955, 77, 5068. doi:10.1021/JA01624A038
32. A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni, Helv. Chim. Acta 1955, 38, 1890. doi:10.1002/HLCA.19550380728
33. For an English translation and commentary, see: A. Eschenmoser, D. Arigoni, Helv. Chim. Acta 2005, 88, 3011. doi:10.1002/HLCA. 200590245
34. P. A. Stadler, A. Eschenmoser, H. Schinz, G. Stork, Helv. Chim. Acta 1957, 40, 2191. doi:10.1002/HLCA.19570400719
35. Key papers include: D. J. Goldsmith, J. Am. Chem. Soc. 1962, 84, 3913. doi:10.1021/JA00879A022
36. D. J. Goldsmith, C. F. Phillips, J. Am. Chem. Soc. 1969, 91, 5862. doi:10.1021/JA01049A028
37. Key papers include: E. E. van Tamelen, J. Willet, M. Schwartz, R. Nadeau, J. Am. Chem. Soc. 1966, 88, 5937.
38. E. E. Van Tamelen, J. P. McCormick, J. Am. Chem. Soc. 1969, 91, 1847. doi:10.1021/JA01035A042
39. E. E. Van Tamelen, T. M. Leiden, J. Am. Chem. Soc. 1982, 104, 2061. doi:10.1021/JA00371A062
40. E. E. Van Tamelen, J. R. Hwu, J. Am. Chem. Soc. 1983, 105, 2490. doi:10.1021/JA00346A073
41. For an early review, see: E. E. Van Tamelen, Acc. Chem. Res. 1968, 1, 111. doi:10.1021/AR50004A003
42. A summary of Johnson's contributions can be found in: W. S. Johnson, A Fifty-Year Love Affair with Organic Chemistry 1998 (American Chemical Society: Washington, DC).
43. For an earlier review, see: W. S. Johnson, Bioorg. Chem. 1976, 5
44. doi:10.1016/0045-2068(76)90016-X
45. For an excellent review of pioneering biomimetic polycyclisation reactions towards terpenoid structures, see: R. A. Yoder, J. N. Johnston, Chem. Rev. 2005, 105, 4730. doi:10.1021/CR040623L
46. Amore recent review: M. Kotora, F. Hessler, B. Eignerova, Eur. J. Org. Chem. 2012, 29. doi:10.1002/EJOC.201100921
47. Key early papers include: E. J. Corey, J. Lee, J. Am. Chem. Soc. 1993, 115, 8873. doi:10.1021/JA00072A064
48. E. J. Corey, J. Lee, D. R. Liu, Tetrahedron Lett. 1994, 35, 9149. doi:10.1016/0040-4039(94)88450-1
49. E. J. Corey, S. Lin, J. Am. Chem. Soc. 1996, 118, 8765. doi:10.1021/JA9620806
50. E. J. Corey, G. Luo, L. S. Lin, J. Am. Chem. Soc. 1997, 119, 9927. doi:10.1021/JA972690L
51. For an impressive recent example, see: K. Surendra, E. J. Corey, J. Am. Chem. Soc. 2009, 131, 13928. doi:10.1021/JA906335U
52. W. J. Zuercher, M. Scholl, R. H. Grubbs, J. Org. Chem. 1998, 63, 4291. doi:10.1021/JO972279G
53. S. P. Maddaford, N. G. Andersen, W. A. Cristofoli, B. A. Keay, J. Am. Chem. Soc. 1996, 118, 10766. doi:10.1021/JA960807K
54. Y. Zhang, G. Z. Wu, G. Agnel, E. I. Negishi, J. Am. Chem. Soc. 1990, 112, 8590. doi:10.1021/JA00179A058
55. M. Bogenstatter, A. Limberg, L. E. Overman, A. L. Tomasi, J. Am. Chem. Soc. 1999, 121, 12206. doi:10.1021/JA9934091
56. M. M. Abelman, L. E. Overman, J. Am. Chem. Soc. 1988, 110, 2328. doi:10.1021/JA00215A068
57. N. E. Carpenter, D. J. Kucera, L. E. Overman, J. Org. Chem. 1989, 54, 5846. doi:10.1021/JO00286A009
58. For a review, see: L. E. Overman, M. M. Abelman, D. J. Kucera, V. D. Tran, D. J. Ricca, Pure Appl. Chem. 1992, 64, 1813. doi:10.1351/PAC199264121813
59. W. Oppolzer, R. J. DeVita, J. Org. Chem. 1991, 56, 6256. doi:10.1021/JO00022A004
60. B. M. Trost, Y. Shi, J. Am. Chem. Soc. 1991, 113, 701. doi:10.1021/JA00002A064
61. B. M. Trost, Y. Shi, J. Am. Chem. Soc. 1992, 114, 791. doi:10.1021/JA00028A074
62. R. L. Funk, K. P. C. Vollhardt, J. Am. Chem. Soc. 1980, 102, 5253. doi:10.1021/JA00536A023
63. S. H. Lecker, N. H. Nguyen, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 856. doi:10.1021/JA00264A059
64. Recent variations on this theme include: M. Petit, C. Aubert, M. Malacria, Org. Lett. 2004, 6, 3937. doi:10.1021/OL0485060
65. U. Groth, N. Richter, A. Kalogerakis, Synlett 2006, 905. doi:10.1055/S-2006-939064
66. Y. W. Andemichael, Y. Huang, K. K. Wang, J. Org. Chem. 1993, 58, 1651. doi:10.1021/JO00059A005
67. J. M. Bao, V. Dragisich, S. Wenglowsky, W. D. Wulff, J. Am. Chem. Soc. 1991, 113, 9873. doi:10.1021/JA00026A036
68. A. Sakakura, A. Ukai, K. Ishihara, Nature 2007, 445, 900. doi:10.1038/NATURE05553
69. S. A. Snyder, D. S. Treitler, A. P. Brucks, J. Am. Chem. Soc. 2010, 132, 14303. doi:10.1021/JA106813S
70. H. Ishibashi, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 11122. doi:10.1021/JA0472026
71. K. Ishihara, S. Nakamura, H. Yamamoto, J. Am. Chem. Soc. 1999, 121, 4906. doi:10.1021/JA984064
72. S. G. Sethofer, T. Mayer, F. D. Toste, J. Am. Chem. Soc. 2010, 132, 8276. doi:10.1021/JA103544P
73. K. Surendra, W. W. Qiu, E. J. Corey, J. Am. Chem. Soc. 2011, 133, 9724. doi:10.1021/JA204142N
74. K. Surendra, E. J. Corey, J. Am. Chem. Soc. 2012, 134, 11992. doi:10.1021/JA305851H
75. Y.-J. Zhao, B. Li, L.-J. S. Tan, Z.-L. Shen, T.-P. Loh, J. Am. Chem. Soc. 2010, 132, 10242. doi:10.1021/JA104119J
76. C. A. Mullen, A. N. Campbell, M. R. Gagne, Angew. Chem. Int. Ed. 2008, 47, 6011. doi:10.1002/ANIE.200801423
77. R. R. Knowles, S. Lin, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 5030. doi:10.1021/JA101256V
78. S. V. Pronin, R. A. Shenvi, Nat. Chem. 2012, 4, 915. doi:10.1038/NCHEM. 1458
79. For recent reviews on radical polycyclisations, see: J. Justicia, L. Alvarez de Cienfuegos, A. G. Campana, D. Miguel, V. Jakoby, A. Gansauer, J. M. Cuerva, Chem. Soc. Rev. 2011, 40, 3525. doi:10.1039/C0CS00220H
80. A. Baralle, A. Baroudi, M. Daniel, L. Fensterbank, J. Goddard, E. Lacôte, M. Larraufie, G. Maestri, M. Malacria, C. Ollivier, in Encyclopedia of Radicals in Chemistry, Biology and Materials (Eds. C. Chatgilialoglu, A. Studer), Ch. 27, pp. 729-765 (Wiley: Chichester).
81. R. Breslow, S. S. Olin, J. T. Groves, Tetrahedron Lett. 1968, 9, 1837. doi:10.1016/S0040-4039(00)76376-3
82. J. Y. Lallemand, M. Julia, D. Mansuy, Tetrahedron Lett. 1973, 14, 4461. doi:10.1016/S0040-4039(01)87249-X
83. Professor Athel Beckwith also made significant contributions to the understanding of the selectivity of radical addition ring closures, including an early radical polycyclisation reaction to form the triquinane framework. A. L. J. Beckwith, C. H. Schiesser, Tetrahedron 1985, 41, 3925. doi:10.1016/S0040- 4020(01)97174-1
84. U. Hoffmann, Y. Gao, B. Pandey, S. Klinge, K. D. Warzecha, C. Krueger, H. D. Roth, M. Demuth, J. Am. Chem. Soc. 1993, 115, 10358. doi:10.1021/JA00075A061
85. X. Xing, M. Demuth, Eur. J. Org. Chem. 2001, 537. doi:10.1002/1099- 0690(200102)2001:3,537::AID-EJOC537.3.0.CO;2-F
86. Acyl selenides as starting materials: L. Chen, G. B. Gill, G. Pattenden, Tetrahedron Lett. 1994, 35, 2593. doi:10.1016/S0040-4039(00)77180-2
87. S. Handa, P. S. Nair, G. Pattenden, Helv. Chim. Acta 2000, 83, 2629. doi:10.1002/1522-2675(20000906)83:9,2629::AID-HLCA2629. 3.0.CO;2-W
88. Macrocyclisation/transannular sequences: for an initial important contribution from Porter, see: N. A. Porter, V. H. T. Chang, D. R. Magnin, B. T. Wright, J. Am. Chem. Soc. 1988, 110, 3554. doi:10.1021/JA00219A034
89. For a review on early developments: S. Handa, G. Pattenden, Contemp. Org. Synth. 1997, 4, 196. doi:10.1039/CO9970400196
90. For recent applications, see: G. Pattenden, M. A. Gonzalez, S. McCulloch, A. Walter, S. J. Woodhead, Proc. Natl. Acad. Sci. USA 2004, 101, 12024. doi:10.1073/PNAS.0401925101
91. G. Pattenden, D. A. Stoker, J. M. Winne, Tetrahedron 2009, 65, 5767. doi:10.1016/J.TET.2009.05.020
92. For reviews, see: A. F. Barrero, J. F. Quilez del Moral, E. M. Sanchez, J. F. Arteaga, Eur. J. Org. Chem. 2006, 1627. doi:10.1002/EJOC.200500849
93. B. B. Snider, Chem. Rev. 1996, 96, 339. doi:10.1021/CR950026M
94. B. B. Snider, J. Y. Kiselgof, B. M. Foxman, J. Org. Chem. 1998, 63, 7945 and references therein. doi:10.1021/JO981238X
95. P. A. Zoretic, Z. Shen, M. Wang, A. A. Ribeiro, Tetrahedron Lett. 1995, 36, 2925 and references therein. doi:10.1016/0040-4039(95) 00433-D
96. A recent example: V. Domingo, J. F. Arteaga, J. L. L. Perez, R. Pelaez, J. F. Q. del Moral, A. F. Barrero, J. Org. Chem. 2012, 77, 341 and references therein. doi:10.1021/JO201968T
97. M. A. Gonzalez, S. Molina-Navarro, J. Org. Chem. 2007, 72, 7462. doi:10.1021/JO0712401
98. For examples, see: Q. Zhang, R. M. Mohan, L. Cook, S. Kazanis, D. Peisach, B. M. Foxman, B. B. Snider, J. Org. Chem. 1993, 58, 7640. doi:10.1021/JO00079A006
99. C. Heinemann, M. Demuth, J. Am. Chem. Soc. 1997, 119, 1129. doi:10.1021/JA962479U
100. D. Yang, X.-Y. Ye, S. Gu, M. Xu, J. Am. Chem. Soc. 1999, 121, 5579. doi:10.1021/JA9901664
101. T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582. doi:10.1126/SCIENCE.1142696
102. S. Rendler, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 5027. doi:10.1021/JA100185P
103. For reviews, see: I. Vilotijevic, T. F. Jamison, Angew. Chem. Int. Ed. 2009, 48, 5250. doi:10.1002/ANIE.200900600
104. F. E. McDonald, R. Tong, J. C. Valentine, F. Bravo, Pure Appl. Chem. 2007, 79, 281. doi:10.1351/PAC200779020281
105. For recent examples, see: A. R. Van Dyke, T. F. Jamison, Angew. Chem. Int. Ed. 2009, 48, 4430. doi:10.1002/ANIE.200900924
106. I. Vilotijevic, T. F. Jamison, Science 2007, 317, 1189. doi:10.1126/SCIENCE.1146421
107. Y. Morimoto,H. Yata, Y. Nishikawa, Angew. Chem. Int. Ed. 2007, 46, 6481. doi:10.1002/ANIE.200701737
108. R. Tong, F. E. McDonald, Angew. Chem. Int. Ed. 2008, 47, 4377. doi:10.1002/ANIE.200800749
109. J. Tanuwidjaja, S.-S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2009, 131, 12084. doi:10.1021/JA9052366
110. M. A. Boone, R. Tong, F. E. McDonald, S. Lense, R. Cao, K. I. Hardcastle, J. Am. Chem. Soc. 2010, 132, 5300. doi:10.1021/JA1006806
111. J. J. Topczewski, J. G. Kodet, D. F. Wiemer, J. Org. Chem. 2011, 76, 909. doi:10.1021/JO1022102
112. Z. Xiong, R. Busch, E. J. Corey, Org. Lett. 2010, 12, 1512. doi:10.1021/OL100213E
113. L. K. Geisler, S. Nguyen, C. J. Forsyth, Org. Lett. 2004, 6, 4159. doi:10.1021/OL048581A
114. For a similar, but less spectacular, synthesis, see: Y. Morimoto, T. Okita, H. Kambara, Angew. Chem. Int. Ed. 2009, 48, 2538. doi:10.1002/ANIE. 200805857
115. For similar recent cascade cyclisations to form polyether natural products, see: P. Yang, P.-F. Li, J. Qu, L.-F. Tang, Org. Lett. 2012, 14, 3932. doi:10.1021/OL3016836
116. J. A. Marshall, R. K. Hann, J. Org. Chem. 2008, 73, 6753. doi:10.1021/JO801188W
117. J. Poulin, C. M. Grise-Bard, L. Barriault, Chem. Soc. Rev. 2009, 38, 3092. doi:10.1039/B819798A
118. W. M. Bandaranayake, J. E. Banfield, D. St. C. Black, J. Chem. Soc., Chem. Commun. 1980, 902. doi:10.1039/C39800000902
119. K. C. Nicolaou, N. A. Petasis, R. E. Zipkin, J. Uenishi, J. Am. Chem. Soc. 1982, 104, 5555. doi:10.1021/JA00384A077
120. K. C. Nicolaou, N. A. Petasis, J. Uenishi, R. E. Zipkin, J. Am. Chem. Soc. 1982, 104, 5557. doi:10.1021/JA00384A078
121. K. C. Nicolaou, R. E. Zipkin, N. A. Petasis, J. Am. Chem. Soc. 1982, 104, 5558. doi:10.1021/JA00384A079
122. K. C. Nicolaou, N. A. Petasis, R. E. Zipkin, J. Am. Chem. Soc. 1982, 104, 5560. doi:10.1021/JA00384A080
123. P. A. Wender, J. J. Howbert, Tetrahedron Lett. 1982, 23, 3983. doi:10.1016/S0040-4039(00)88675-X
124. K. C. Nicolaou, D. Sarlah, T. R. Wu, W. Zhan, Angew. Chem. Int. Ed. 2009, 48, 6870. doi:10.1002/ANIE.200903382
125. S. D. Tilley, K. P. Reber, E. J. Sorensen, Org. Lett. 2009, 11, 701. doi:10.1021/OL802768P
126. D. A. Vosburg, C. D. Vanderwal, E. J. Sorensen, J. Am. Chem. Soc. 2002, 124, 4552. doi:10.1021/JA025885O
127. D. A. Evans, J. T. Starr, Angew. Chem. 2002, 114, 1865. doi:10.1002/1521-3757(20020517)114:10,1865::AID-ANGE1865.3.0.CO;2-6
128. N. Tanaka, T. Suzuki, T. Matsumura, Y. Hosoya, M. Nakada, Angew. Chem. Int. Ed. 2009, 48, 2580. doi:10.1002/ANIE.200900097
129. S. E. Denmark, R. Y. Baiazitov, S. T. Nguyen, Tetrahedron 2009, 65, 6535. doi:10.1016/J.TET.2009.05.060
130. D. M. Hodgson, A. H. Labande, F. Y. T. M. Pierard, M.A. Exposito Castro, J. Org. Chem. 2003, 68, 6153. doi:10.1021/JO0343735
131. A. Padwa, S. P. Carter, H. Nimmesgern, J. Org. Chem. 1986, 51, 1157. doi:10.1021/JO00357A050
132. A. Padwa, Chem. Soc. Rev. 2009, 38, 3072. doi:10.1039/B816701J
133. A. Padwa, Tetrahedron 2011, 67, 8057. doi:10.1016/J.TET.2011. 07.009
134. Carbenoids have also found use in different domino polycyclisation strategies, such as that recently employed to synthesise (-)-minfiensine and (-)-vincorine. M. Zhang, X. Huang, L. Shen, Y. Qin, J. Am. Chem. Soc. 2009, 131, 6013. doi:10.1021/JA901219V
135. Y. Sasaki, D. Kato, D. L. Boger, J. Am. Chem. Soc. 2010, 132, 13533. doi:10.1021/JA106284S
136. E. L. Campbell, A. M. Zuhl, C. M. Liu, D. L. Boger, J. Am. Chem. Soc. 2010, 132, 3009. doi:10.1021/JA908819Q
137. C. H. Heathcock, M. M. Hansen, R. B. Ruggeri, J. C. Kath, J. Org. Chem. 1992, 57, 2544. doi:10.1021/JO00035A008
138. C. H. Heathcock, Proc. Natl. Acad. Sci. USA 1996, 93, 14323. doi:10.1073/PNAS.93.25.14323
139. F. He, Y. Bo, J. D. Altom, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 6771. doi:10.1021/JA9915201
140. J. M. Mejia-Oneto, A. Padwa, Org. Lett. 2006, 8, 3275. doi:10.1021/OL061137I
141. D. F. Fischer, R. Sarpong, J. Am. Chem. Soc. 2010, 132, 5926. doi:10.1021/JA101893B
142. C. L. Martin, L. E. Overman, J. M. Rohde, J. Am. Chem. Soc. 2010, 132, 4894. doi:10.1021/JA100178U
143. T. Hudlicky, J. W. Reed, The Way of Synthesis, 1st ed. 2007 (Wiley- VCH: Weinheim).
144. S. P. Lathrop, T. Rovis, J. Am. Chem. Soc. 2009, 131, 13628. doi:10.1021/JA905342E
145. For a classification and review of these types of transformation, see: D. E. Fogg, E. N. dos Santos, Coord. Chem. Rev. 2004, 248, 2365. doi:10.1016/J.CCR.2004.05.012
146. K. C. Nicolaou, Y. H. Lim, J. Becker, Angew. Chem. Int. Ed. 2009, 48, 3444. doi:10.1002/ANIE.200900058
147. Y. Zeng, J. Aube, J. Am. Chem. Soc. 2005, 127, 15712. doi:10.1021/JA055629M
148. G. Majetich, Y. Zhang, X. Tian, J. E. Britton, Y. Li, R. Phillips, Tetrahedron 2011, 67, 10129. doi:10.1016/J.TET.2011.09.072
149. R. M. A. Lavigne, M. Riou, M. L. Girardin, L. Morency, L. Barriault, Org. Lett. 2005, 7, 5921. doi:10.1021/OL0527072
150. S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 475, 183. doi:10.1038/NATURE10232
151. O. L. Chapman, M. R. Engel, J. P. Springer, J. C. Clardy, J. Am. Chem. Soc. 1971, 93, 6696. doi:10.1021/JA00753A073
152. Rugulosin: K. C. Nicolaou, Y. H. Lim, C. D. Papageorgiou, J. L. Piper, Angew. Chem. 2005, 117, 8131. doi:10.1002/ANGE. 200503678
153. Thiostrepton: K. C. Nicolaou, M. Zak, B. S. Safina, A. A. Estrada, S. H. Lee, M. Nevalainen, J. Am. Chem. Soc. 2005, 127, 11176. doi:10.1021/JA052934Z
154. K. C. Nicolaou, B. S. Safina, M. Zak, S. H. Lee, M. Nevalainen, M. Bella, A. A. Estrada, C. Funke, F. J. Zecri, S. Bulat, J. Am. Chem. Soc. 2005, 127, 11159. doi:10.1021/JA0529337
155. P. D. Brown, A. C. Willis, M. S. Sherburn, A. L. Lawrence, Org. Lett. 2012, 14, 4537. doi:10.1021/OL302042U
156. W. Liu, V. Khedkar, B. Baskar, M. Schuermann, K. Kumar, Angew. Chem. Int. Ed. 2011, 50, 6900. doi:10.1002/ANIE.201102440
157. C. de Graaff, E. Ruijter, R. V. A. Orru, Chem. Soc. Rev. 2012, 41, 3969. doi:10.1039/C2CS15361K
158. S. S. vanBerkel, B.G. M.Bogels,M.A.Wijdeven, B.Westermann, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2012, 3543. doi:10.1002/EJOC. 201200030
159. E. Ruijter, R. Scheffelaar, R. V. A. Orru, Angew. Chem. Int. Ed. 2011, 50, 6234. doi:10.1002/ANIE.201006515
160. D. Enders, C. Grondal, M. R. M. Huettl, Angew. Chem. Int. Ed. 2007, 46, 1570. doi:10.1002/ANIE.200603129
161. D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602. doi:10.1002/ANIE.200460548
162. A. Strecker, Justus Liebigs Ann. Chem. 1850, 75, 27. doi:10.1002/JLAC. 18500750103
163. A. Hantzsch, Ber. Dtsch. Chem. Ges. 1881, 14, 1637. doi:10.1002/CBER. 18810140214
164. P. Biginelli, Ber. Dtsch. Chem. Ges. 1891, 24, 1317. doi:10.1002/CBER. 189102401228
165. A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552. doi:10.1021/JA026216D
166. A. Domling, Chem. Rev. 2006, 106, 17. doi:10.1021/CR0505728
167. Combining MCRs with other processes leads to some even more effective multi-bond forming processes. Some recent notable examples include: A. Znabet, J. Zonneveld, E. Janssen, F. J. J. De Kanter, M. Helliwell, N. J. Turner, E. Ruijter, R. V. A. Orru, Chem. Commun. 2010, 46, 7706.
168. N. Elders, D. van der Born, L. J. D. Hendrickx, B. J. J. Timmer, A. Krause, E. Janssen, F. J. J. deKanter, E. Ruijter, R. V. A. Orru, Angew. Chem. Int. Ed. 2009, 48, 5856.
169. H. Mizoguchi, H. Oguri, K. Tsuge, H. Oikawa, Org. Lett. 2009, 11, 3016.
170. N. Kumagai, G. Muncipinto, S. L. Schreiber, Angew. Chem. Int. Ed. 2006, 45, 3635.
171. Synthesis using more than one MCR: O. Pando, S. Stark, A. Denkert, A. Porzel, R. Preusentanz, L. A. Wessjohann, J. Am. Chem. Soc. 2011, 133, 7692. doi:10.1021/JA2022027
172. For recent reviews on organocatalytic multi-bond forming processes, see: C. M. Marson, Chem. Soc. Rev. 2012, 41, 7712. doi:10.1039/C2CS35183H
173. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167. doi:10.1038/NCHEM.539
174. H. Pellissier, Adv. Synth. Catal. 2012, 354, 237. doi:10.1002/ADSC. 201100714
175. D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441
176. doi:10.1038/NATURE04820
177. For reviews on asymmetric multicatalytic processes, see: J. Zhou, Chem. Asian J. 2010, 5, 422.
178. R. C. Wende, P. R. Schreiner, Green Chem. 2012, 14, 1821.
179. See also ref 88].
180. For an interesting recent development in multifunctional catalyst design, see:Y. Chi, S. T. Scroggins, J. M. J. Frechet, J. Am. Chem. Soc. 2008, 130, 6322. doi:10.1021/JA8013456
181. D. Enders, M. R. M. Huttl, G. Raabe, J. W. Bats, Adv. Synth. Catal. 2008, 350, 267. doi:10.1002/ADSC.200700396
182. For some interesting novel examples featuring dipolar cycloadditions, see: P. Garner, H. U. Kaniskan, C. M. Keyari, L. Weerasinghe, J. Org. Chem. 2011, 76, 5283. doi:10.1021/JO200553G
183. P. Garner, L. Weerasinghe, W. J. Youngs, B. Wright, D. Wilson, D. Jacobs, Org. Lett. 2012, 14, 1326. doi:10.1021/OL3002128
184. For a combination of metal cycloisomerisation and a Diels-Alder reaction, see: C. F. Bender, F. K. Yoshimoto, C. L. Paradise, J. K. D. Brabander, J. Am. Chem. Soc. 2009, 131, 11350. doi:10.1021/JA905387R
185. E. Knoevenagel, Ber. Dtsch. Chem. Ges. 1898, 31, 2596. doi:10.1002/CBER.18980310308
186. For examples, see (and references therein): L. F. Tietze, Y. Zhou, Angew. Chem. Int. Ed. 1999, 38, 2045.
187. L. F. Tietze, N. Bohnke, S. Dietz, Org. Lett. 2009, 11, 2948.
188. A. L. Lawrence, R. M. Adlington, J. E. Baldwin, V. Lee, J. A. Kershaw, A. L. Thompson, Org. Lett. 2010, 12, 1676.
189. Y. Gao, G.-Q. Wang, K. Wei, P. Hai, F. Wang, J.-K. Liu, Org. Lett. 2012, 14, 5936.
190. L. F. Tietze, J. Heterocycl. Chem. 1990, 27, 47.
191. P. R. Nandaluru, G. J. Bodwell, Org. Lett. 2012, 14, 310. doi:10.1021/OL2030636
192. C. A. Carson, M. A. Kerr, Angew. Chem. Int. Ed. 2006, 45, 6560. doi:10.1002/ANIE.200602569
193. I. S. Young, M. A. Kerr, J. Am. Chem. Soc. 2007, 129, 1465. doi:10.1021/JA068047T
194. P. Jakubec, A. Hawkins, W. Felzmann, D. J. Dixon, J. Am. Chem. Soc. 2012, 134, 17482. doi:10.1021/JA308826X
195. For an excellent review, see: B. B. Toure, D. G. Hall, Chem. Rev. 2009, 109, 4439. doi:10.1021/CR800296P
196. Recent discoveries and new applications are paving the way for future work. For some recent targeted syntheses involving a key MCR, see: T. Ritthiwigrom, S. G. Pyne, Org. Lett. 2008, 10, 2769.
197. T. Ritthiwigrom, A. C. Willis, S. G. Pyne, J. Org. Chem. 2009, 75, 815.
198. L.V. Frolova,N.M. Evdokimov, K. Hayden, I.Malik, S. Rogelj, A. Kornienko, I. V. Magedov, Org. Lett. 2011, 13, 1118.
199. Y. Inoue, K. Ohuchi, I. F. Yen, S. Imaizumi, Bull. Chem. Soc. Jpn. 1989, 62, 3518. doi:10.1246/BCSJ.62.3518
200. K. C. Nicolaou, D. Sarlah, D. M. Shaw, Angew. Chem. Int. Ed. 2007, 46, 4708. doi:10.1002/ANIE.200701552
201. For a review on other MCRs involving CO, see: M. D. Mihovilovic, P. Stanetty, Angew. Chem. Int. Ed. 2007, 46, 3612. doi:10.1002/ANIE.200604743
202. T. Tanino, S. Ichikawa, M. Shiro, A. Matsuda, J. Org. Chem. 2010, 75, 1366. doi:10.1021/JO9027193
203. W. Wang, S. Joyner, K. A. S. Khoury, A. Doemling, Org. Biomol. Chem. 2010, 8, 529. doi:10.1039/B918214D
204. E. Aviles, A. D. Rodriguez, Org. Lett. 2010, 12, 5290. doi:10.1021/OL102351Z
205. J. Isaacson, Y. Kobayashi, Angew. Chem. Int. Ed. 2009, 48, 1845. doi:10.1002/ANIE.200805709
206. S. Takiguchi, T. Iizuka, Y.-s. Kumakura, K. Murasaki, N. Ban, K. Higuchi, T. Kawasaki, J. Org. Chem. 2010, 75, 1126. doi:10.1021/JO9023107
207. T. Iizuka, S. Takiguchi, Y.-s. Kumakura, N. Tsukioka, K. Higuchi, T. Kawasaki, Tetrahedron Lett. 2010, 51, 6003. doi:10.1016/J.TET LET.2010.09.026
208. A. Znabet, M. M. Polak, E. Janssen, F. J. J. de Kanter, N. J. Turner, R. V. A. Orru, E. Ruijter, Chem. Commun. 2010, 46, 7918. doi:10.1039/C0CC02823A
209. Y. Yip, F. Victor, J. Lamar, R. Johnson, Q. M. Wang, D. Barket, J. Glass, L. Jin, L. Liu, D. Venable, M. Wakulchik, C. Xie, B. Heinz, E. Villarreal, J. Colacino, N. Yumibe, M. Tebbe, J. Munroe, S.-H. Chen, Bioorg. Med. Chem. Lett. 2004, 14, 251. doi:10.1016/J.BMCL.2003.09.074
210. J. A. Monn, M. J. Valli, J. Org. Chem. 1994, 59, 2773. doi:10.1021/JO00089A022
211. For some recent impressive 'one-pot' examples, see: N. Chernyak, V. Gevorgyan, Angew. Chem. Int. Ed. 2010, 49, 2743. doi:10.1002/ANIE.200907291
212. B.-C. Hong, P. Kotame, C.-W. Tsai, J.-H. Liao, Org. Lett. 2010, 12, 776. doi:10.1021/OL902840X
213. T. Sakaguchi, S. Kobayashi, S. Katsumura, Org. Biomol. Chem. 2011, 9, 257. doi:10.1039/C0OB00627K
214. For a recent application of the 'one-pot' strategy applied in industry, see: F. Xu, M. Zacuto, N. Yoshikawa, R. Desmond, S. Hoerrner, T. Itoh, M. Journet, G. R. Humphrey, C. Cowden, N. Strotman, P. Devine, J. Org. Chem. 2010, 75, 7829. doi:10.1021/JO101704B
215. H. Ishikawa, M. Honma, Y. Hayashi, Angew. Chem. Int. Ed. 2011, 50, 2824. doi:10.1002/ANIE.201006204
216. H. Ishikawa, T. Suzuki, Y. Hayashi, Angew. Chem. Int. Ed. 2009, 48, 1304. doi:10.1002/ANIE.200804883
217. B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. Int. Ed. 2009, 48, 4349. doi:10.1002/ANIE.200900220
218. For another recent example of the combination of organocatalysis and metal catalysis, see: W. Sun, G. Zhu, L. Hong, R. Wang, Chem.- Eur. J. 2011, 17, 13958. doi:10.1002/CHEM.201103083
219. H. Duckert, V. Pries, V. Khedkar, S. Menninger, H. Bruss, A. W. Bird, Z. Maliga, A. Brockmeyer, P. Janning, A. Hyman, S. Grimme, M. Schuermann, H. Preut, K. Huebel, S. Ziegler, K. Kumar, H. Waldmann, Nat. Chem. Biol. 2012, 8, 179. doi:10.1038/NCHEMBIO.758
220. For some recent examples of the use of two-directional synthesis of symmetrical targets, see: R. Barth, J. Mulzer, Angew. Chem. 2007, 119, 5893. doi:10.1002/ANGE.200701065
221. K. M. G. O'Connell, H. S. G. Beckmann, L. Laraia, H. T. Horsley, A. Bender, A. R. Venkitaraman, D. R. Spring, Org. Biomol. Chem. 2012, 10, 7545. doi:10.1039/C2OB26272J
222. K. C. Nicolaou, S. Totokotsopoulos, D. Giguere, Y.-P. Sun, D. Sarlah, J. Am. Chem. Soc. 2011, 133, 8150. doi:10.1021/JA2032635
223. Y. Morimoto, M. Takaishi, N. Adachi, T. Okita, H. Yata, Org. Biomol. Chem. 2006, 4, 3220. doi:10.1039/B608098G
224. Terminus differentiation techniques have been neatly classified by Schreiber: C. S. Poss, S. L. Schreiber, Acc. Chem. Res. 1994, 27, 9.
225. For a review, see: S. R. Magnuson, Tetrahedron 1995, 51, 2167. doi:10.1016/0040-4020(94)01070-G
226. N. Ikemoto, S. L. Schreiber, J. Am. Chem. Soc. 1992, 114, 2524. doi:10.1021/JA00033A029
227. C. S. Poss, S. D. Rychnovsky, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 3360. doi:10.1021/JA00061A057
228. Y. Zhang, C. C. Arpin, A. J. Cullen, M. J. Mitton-Fry, T. Sammakia, J. Org. Chem. 2011, 76, 7641. doi:10.1021/JO2012658
229. Y. Wang, O. Kataeva, P. Metz, Adv. Synth. Catal. 2009, 351, 2075. doi:10.1002/ADSC.200900295
230. E. W. Rogers, T. F. Molinski, J. Org. Chem. 2009, 74, 7660. doi:10.1021/JO901007V
231. N. R. Norcross, J. P. Melbardis, M. F. Solera, M. A. Sephton, C. Kilner, L. N. Zakharov, P. C. Astles, S. L. Warriner, P. R. Blakemore, J. Org. Chem. 2008, 73, 7939. doi:10.1021/JO8013512
232. J. M. Holland, M. Lewis, A. Nelson, J. Org. Chem. 2003, 68, 747. doi:10.1021/JO026456B
233. C. J. Exner, M. Turks, F. Fonquerne, P. Vogel, Chem.-Eur. J. 2011, 17, 4246. doi:10.1002/CHEM.201003264
234. D. Robbins, A. F. Newton, C. Gignoux, J.-C. Legeay, A. Sinclair, M. Rejzek, C. A. Laxon, S. K. Yalamanchili, W. Lewis, M. A. O'Connell, R. A. Stockman, Chem. Sci. 2011, 2, 2232. doi:10.1039/C1SC00371B
235. A. F. Newton, S. J. Roe, J.-C. Legeay, P. Aggarwal, C. Gignoux, N. J. Birch, R. Nixon, M.-L. Alcaraz, R. A. Stockman, Org. Biomol. Chem. 2009, 7, 2274. doi:10.1039/B907720K
236. P. Aggarwal, G. Procopiou, D. Robbins, G. Harbottle, W. Lewis, R. A. Stockman, Synlett 2012, 423.
237. C. Gignoux, A. F. Newton, A. Barthelme, W. Lewis, M.-L. Alcaraz, R. A. Stockman, Org. Biomol. Chem. 2012, 10, 67. doi:10.1039/C1OB06380D
238. D. Liu, H. P. Acharya, M. Yu, J. Wang, V. S. C. Yeh, S. Kang, C. Chiruta, S. M. Jachak, D. L. J. Clive, J. Org. Chem. 2009, 74, 7417. doi:10.1021/JO901481N
239. B. B. Liau, B. C. Milgram, M. D. Shair, J. Am. Chem. Soc. 2012, 134, 16765. doi:10.1021/JA307207Q
240. For another recent example of two-fold reaction sequences on pseudo-symmetrical substrates, see: E. Airiau, T. Spangenberg, N. Girard, B. Breit, A. Mann, Org. Lett. 2010, 12, 528. doi:10.1021/OL902718Q
241. J. A. Berson, Tetrahedron 1992, 48, 3. doi:10.1016/S0040-4020(01) 80574-3
242. M. Potowski, M. Schurmann, H. Preut, A. P. Antonchick, H. Waldmann, Nat. Chem. Biol. 2012, 8, 428. doi:10.1038/NCHEM BIO.901
243. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243. doi:10.1038/NATURE06351
244. J. S. Clark, M. C. Kimber, J. Robertson, C. S. P. McErlean, C. Wilson, Angew. Chem. Int. Ed. 2005, 44, 6157. doi:10.1002/ANIE. 200501925
245. J. S. Clark, O. Hamelin, Angew. Chem. Int. Ed. 2000, 39, 372. doi:10.1002/(SICI)1521-3773(20000117)39:2,372::AID-ANIE372. 3.0.CO;2-Y
246. Y. Zhang, J. D. Rainier, Org. Lett. 2009, 11, 237. doi:10.1021/OL8025439
247. G. Matsuo, K. Kawamura, N. Hori, H. Matsukura, T. Nakata, J. Am. Chem. Soc. 2004, 126, 14374. doi:10.1021/JA0449269
248. C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354. doi:10.1021/JO982098U
249. K. C. Nicolaou, D. G. McGarry, P. K. Sommers, J. Am. Chem. Soc. 1990, 112, 3696. doi:10.1021/JA00165A085
250. J. L. Ravelo, A. Regueiro, J. D. Martin, Tetrahedron Lett. 1992, 33, 3389. doi:10.1016/S0040-4039(00)92096-3
251. For a recent example from the same laboratory, see: B. Cheng, J. D. Sunderhaus, S. F. Martin, Org. Lett. 2010, 12, 3622. doi:10.1021/OL101356U
252. K. S. Feldman, B. K. Selfridge, Org. Lett. 2012, 14, 5484. doi:10.1021/OL302567F
253. M. W. B. Pfeiffer, A. J. Phillips, J. Am. Chem. Soc. 2005, 127, 5334. doi:10.1021/JA0509836
254. D. Morton, S. Leach, C. Cordier, S. Warriner, A. Nelson, Angew. Chem. Int. Ed. 2009, 48, 104. doi:10.1002/ANIE.200804486
255. S.-H. Kim, N. Bowden, R. H. Grubbs, J. Am. Chem. Soc. 1994, 116, 10801. doi:10.1021/JA00102A062
256. S.-H. Kim, W. J. Zuercher, N. B. Bowden, R. H. Grubbs, J. Org. Chem. 1996, 61, 1073. doi:10.1021/JO951648A
257. W. J. Zuercher, M. Scholl, R. H. Grubbs, J. Org. Chem. 1998, 63, 4291. doi:10.1021/JO972279G
258. For reviews, see: S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317. doi:10.1021/CR020009E
259. M. Mori, Adv. Synth. Catal. 2007, 349, 121. doi:10.1002/ADSC. 200600484
260. J. Li, D. Lee, Eur. J. Org. Chem. 2011, 4269. doi:10.1002/EJOC. 201100438
261. L. Chang, H. Jiang, J. Fu, B. Liu, C.-c. Li, Z. Yang, J. Org. Chem. 2012, 77, 3609. doi:10.1021/JO300039Q
262. Y. Adachi, N. Kamei, S. Yokoshima, T. Fukuyama, Org. Lett. 2011, 13, 4446. doi:10.1021/OL2018032
263. M. Schubert, P. Metz, Angew. Chem. Int. Ed. 2011, 50, 2954. doi:10.1002/ANIE.201007551
264. H. Oguri, T. Hiruma, Y. Yamagishi, H. Oikawa, A. Ishiyama, K. Otoguro, H. Yamada, S. Omura, J. Am. Chem. Soc. 2011, 133, 7096. doi:10.1021/JA200374Q
265. D. S. Siegel, G. Piizzi, G. Piersanti, M. Movassaghi, J. Org. Chem. 2009, 74, 9292. doi:10.1021/JO901926Z
266. J. Ramharter, H.Weinstabl, J. Mulzer, J. Am. Chem. Soc. 2010, 132, 14338. doi:10.1021/JA107533M
267. S. Mukherjee, D. Lee, Org. Lett. 2009, 11, 2916. doi:10.1021/OL900923C
268. Metathesis also features in some impressive, enantioselective domino sequences, for reviews see: S. Kress, S. Blechert, Chem. Soc. Rev. 2012, 41, 4389. doi:10.1039/C2CS15348C
269. A. H. Hoveyda, S. J. Malcolmson, S. J. Meek, A. R. Zhugralin, Angew. Chem. Int. Ed. 2010, 49, 34. doi:10.1002/ANIE.200904491 170]
270. D. Banti, M. North, Tetrahedron Lett. 2002, 43, 1561. doi:10.1016/S0040-4039(02)00009-6
271. D. Banti, M. North, Adv. Synth. Catal. 2002, 344, 694. doi:10.1002/1615-4169(200208)344:6/7,694::AID-ADSC694. 3.0.CO;2-X
272. For an even more recent example of the combined metathesis- Diels-Alder approach, see: A. Aljarilla, M. C. Murcia, A. G. Csaky, J. Plumet, Eur. J. Org. Chem. 2009, 822. doi:10.1002/EJOC. 200800936
273. J. A. Enquist, B. M. Stoltz, Nature 2008, 453, 1228. doi:10.1038/ NATURE07046
274. J. Tsuji, I. Minami, I. Shimizu, Tetrahedron Lett. 1983, 24, 1793. doi:10.1016/S0040-4039(00)81772-4
275. B. M. Trost, T. J. Fullerton, J. Am. Chem. Soc. 1973, 95, 292. doi:10.1021/JA00782A080
276. J. A. Enquist, S. C. Virgil, B. M. Stoltz, Chem.-Eur. J. 2011, 17, 9957. doi:10.1002/CHEM.201100425
277. The syntheses of dendrimers provide examples of high order multidirectional synthesis. For a review, see: T. Iizuka, S. Takiguchi, Y.-s. Kumakura, N. Tsukioka, K. Higuchi, T. Kawasaki, Tetrahedron Lett. 2010, 51, 6003. doi:10.1016/J.TETLET.2010.09.026
278. H. Hopf, M. S. Sherburn, Angew. Chem. Int. Ed. 2012, 51, 2298. doi:10.1002/ANIE.201102987
279. G. Bojase, T. V. Nguyen, A. D. Payne, A. C. Willis, M. S. Sherburn, Chem. Sci. 2011, 2, 229. doi:10.1039/C0SC00500B
280. G. A. Crispino, P. T. Ho, K. B. Sharpless, Science 1993, 259, 64. doi:10.1126/SCIENCE.8418495
281. From an achiral starting material, an enantiomeric ratio of approximately 105 : 1 is generated by virtue of an effect known as the Horeau principle: See W. Langenbeck, G. Triem, Z. Physik. Chem. 1936, A177, 401.
282. J. P. Vigneron, M. Dhaenens, A. Horeau, Tetrahedron 1973, 29, 1055. doi:10.1016/0040-4020(73)80060-2
283. V. Rautenstrauch, Bull. Soc. Chim. Fr. 1994, 131, 515.
284. D. S. Glueck, Catal. Sci. Technol. 2011, 1, 1099. doi:10.1039/C1CY00048A
285. For a recent example of this effect in independent reactions, see: S. Bell, B. Wustenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz, Science 2006, 311, 642. doi:10.1126/SCIENCE.1121977
286. Z. Xiong, E. J. Corey, J. Am. Chem. Soc. 2000, 122, 9328. doi:10.1021/JA0024901
287. I. Paterson, E. A. Anderson, S. M. Dalby, J. H. Lim, P. Maltas, C. Moessner, Chem. Commun. 2006, 4186. doi:10.1039/B612697A
288. A second-generation synthesis has recently been completed utilising this methodology: I. Paterson, P. Maltas, S. M. Dalby, J. H. Lim, E. A. Anderson, Angew. Chem. Int. Ed. 2012, 51, 2749. doi:10.1002/ANIE.201108594
289. C. H. Heathcock, Angew. Chem. Int. Ed. Engl. 1992, 31, 665. doi:10.1002/ANIE.199206653