Copper-catalyzed asymmetric allylic alkylation of halocrotonates: Efficient synthesis of versatile chiral multifunctional building blocks

Advanced Synthesis and Catalysis

Volumn 352, Issue 6, 2010, Pages 999-1013

  Den Hartog, Tim ^a   Macia, Beatriz ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Asymmetric catalysis; Carbon carbon bond formation; Copper catalysis; Grignard reagents; Multifunctional building blocks

Indexed keywords

EID: 77951189111     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000109     Document Type: Article

References (136)

1. a) S. Warren, Organic Synthesis: The Disconnection Approach, Wiley, Chichester, 1982;
2. b) S. Hanessian, in: Total Synthesis of Natural Products: The 'Chiron' Approach, Organic Chemistry Series, (Ed. : X E. Baldwin), Pergamon: Oxford, 1983; Vol.3;
3. c)E.X Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989;
4. d) K. C. Nicolaou, E.J. Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods, VCH, Weinheim, 1996;
5. e) K. C. Nicolaou, S. A. Snyder, Classics in Total Synthesis II: More Targets, Strategies, Methods; Wiley-VCH, Weinheim, 2003.
6. a) Z. Lu, S. Ma, Angew. Chem. 2008, 720, 264-303;
7. Angew. Chem. Int. Ed. 2008, 47, 258-297;
8. b) K. Geurts, S. P. Fletcher, A. W. van Zijl, A. X Minnaard, B. L. Feringa, Pure Appl. Chem. 2008, 80, 1025-1037;
9. c) S. R. Harutyunyan, T. den Hartog, K. Geurts, A. X Minnaard, B. L. Feringa, Chem. Rev. 2008, 108, 2824-2852;
10. d) A. Alexakis, X E. Bäckvall, N. Krause, O. Pàmies, M. Dièguez, Chem. Rev. 2008, 108, 2796-2823;
11. e) C. A. Falciola, A. Alexakis, Eur. J. Org. Chem. 2008, 3765-3780.
12. a) H. Leuser, S. Perrone, F. Liron, F. F. Kneisel, P. Knochel, Angew. Chem. 2005, 44, 4703-4707;
13. Angew. Chem. Int. Ed. 2005, 44, 4627-4631;
14. b) A.W. van Zijl, F. López, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2007, 72, 2558-2563;
15. c) T. Reiss, B. Breit, Chem. Eur. J. 2009,72, 6345-6348.
16. a) A. W. van Zijl, F. López, A. X Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420;
17. b) F. López, A. W. van Zijl, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2006, 409-411;
18. c) K. Geurts, S. P. Fletcher, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 15572-15573;
19. d) A. W van Zijl, W Szymanski, F. López, A. X Minnaard, B. L. Feringa, J. Org. Chem. 2008, 73, 6994-7002.
20. a) B. L. Feringa, R. Badorrey, D. Peña, S. R. Harutyunyan, A. X Minnaard, Proc. Natl. Acad. Sci. USA 2004, 101, 5834-5838;
21. b) F. López, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2004, 126, 12784-12875;
22. c) F. López, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa, Angew. Chem. 2005, 117, 2812-2816;
23. Angew. Chem. Int. Ed. 2005, 44, 27522756;
24. d) R. DesMazery, M. Pullez, F López, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 9966-9967;
25. e)B. Maciá Ruiz, K. Geurts, M. A. Fernández- Ibáñez, B. ter Horst, A. J. Minnaard, B. L. Feringa, Org. Lett. 2007, 9, 5123-5126;
26. f) B. Maciá, M. A. Fernández-Ibáñez, M. Mršič, A. J. Minnaard, B. L. Feringa, Tetrahedron Lett. 2008, 49, 1877-1880;
27. g) M. A. Fernández-Ibáñez, B. Maciá, M. G. Pizzuti, A. J. Minnaard, B. L. Feringa, Angew. Chem. 2009, 727, 9503-9505;
28. Angew. Chem. Int. Ed. 2009, 48, 9339-9341;
29. h) F. López, A. X Minnaard, B. L. Feringa, Ace. Chem. Res. 2007, 40, 179-188;
30. i) T. Jerphagnon, M. G. Pizzuti, A. X Minnaard, B. L. Feringa, Chem. Soc. Rev. 2009, 38, 1039-1075.
31. T. den Hartog, S. R. Harutyunyan, D. Font, A. X Minnaard, B. L. Feringa, Angew. Chem. 2008, 120, 404-407;
32. Angew. Chem. Int. Ed 2008, 47, 398-401.
33. a) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691;
34. b) K. E. Murphy, A. H. Hoveyda, Org. Lett. 2005, 7, 1255-1258;
35. c)Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2006, 128, 15604-15605.
36. th 2010) identified 1563 natural products for a-Me-butyric acid with either a single or double bond and free sites at both the 4-position and the carboxylic acid moiety.
37. For recent selected examples of the synthesis of a-Mecarbonyls see: a) S.-M. Lei, C. Boim, Angew. Chem. 2008, 120, 9052-9055;
38. Angew. Chem. Int. Ed. 2008, 47, 8920-8923;
39. b) C. Studte, B. Breit, Angew. Chem. 2008, 120, 5531-5535;
40. Angew. Chem. Int. Ed. 2008, 47, 54515455;
41. c)K. Zhang, Q. Peng, X.-L. Hou, Y.-D. Wu, Angew. Chem. 2008, 120, 1765-1768;
42. Angew. Chem. Int. Ed. 2008, 47, 1741-1744;
43. d) S. Li, S. F. Zhu, C.-M. Zhang, Q.-L. Zhou, J. Am. Chem. Soc. 2008, 130, 8584-8585;
44. e) L. Qui, Y-M. Li, F Y Kwong, W.-Y. Yu, Q.-H. Fan, A. S. C. Chan, Adv. Synth. Catal. 2007, 349, 517-520;
45. f) X Zhou, X W. Ogle, Y. Fan, V. Banphavichit, Y Zhu, K. Burgess, Chem. Eur. J. 2007, 13, 7162-7170.
46. This substrate was chosen mainly due to its physical properties (i.e., UV activity and low volatility).
47. [3b] on (E)-[(4-bromobut-2-enyloxy)methyl]benzene might be performed, followed by deprotection of the hydroxy group and finally Jones oxidation as described in: T. Tashiro, K. Mori, Eur. J. Org. Chem. 1999, 2167-2173.
48. |7cl (up to 28% yield).
49. The formation of the cyclopropane product 8b can be optimized and will be reported in due course.
50. Benzyl crotonate is formed via Br-Mg exchange and subsequent quenching during work-up. Studies on this reagent will be disclosed shortly.
51. The reaction has been performed at 10 mmol scale as well and gave 88% yield and 96% ee. By improving the experimental conditions (presumably longer addition of the substrate to the reaction mixture is required) higher ee might be obtained.
52. Apparently allowing the reaction to proceed for 40 h gives slightly lower yield. The slightly lower ee might be explained by analysis issues due to overlapping of the large first peak and small second peak for this enantiomer on the chiral HPLC.
53. T. Tashiro, K. Mori, Eur. J. Org. Chem. 1999, 2167-2173.
54. T. Tachihara, S. Ishizaki, Y Kurobayashi, H. Tamura, Y Ikemoto, A. Onuma, T. Kitahara, Flavour Fragrance J. 2003, 75, 305-308.
55. This building block has also been obtained by a) hydrogenation in 72% ee: M. Schönleber, R. Hilgraf, A. Pfaltz, Adv. Synth. Catal. 2008, 350, 2033-2038;
56. [9b];
57. d) enzymatic synthesis: K.-H. Engel, J. Am. Oil Chem. Soc. 1992, 69, 146150.
58. [9e]
59. C. Smit, M. W Fraaije, A. X Minnaard, J. Org. Chem. 2008, 73, 9482-9485.
60. This product has been prepared before using an enzymatic method: M. Bakke, H. Ohta, U. Kazmaier, T. Sugai, Synthesis 1999, 1671-1677.
61. With respect to the higher ee measured for the iodolactonization products (vide infra) there might be a small impurity under the minor peak on the chiral GC and the ee might be higher.
62. G. T. Pearce, W. E. Gore, R. M. Silverstein, J. Org. Chem. 1976, 41, 2797-2803.
63. This building block has been obtained a) from the chiral pool: see ref.[181; b) enzymatically: D. V. Patel, F. VanMiddlesworth, X Donaubauer, P. Gannett, C. J. Sih, J. Am. Chem. Soc. 1986, 108, 4603-4614;
64. c) using Sharpless AD and further elaboration: H. A. Vaccaro, D. E. Levy, A. Sawabe, T. Jaetsch, S. Masamune, Tetrahedron Lett. 1992, 33, 1937-1940;
65. d) using a chiral auxiliary: R. Bajpai, F. Yang, D. P. Curran, Tetrahedron Lett. 2007, 48, 7965-7968.
66. Storage of 12 for extended time at -20̈C (checked after 7 days) also gives lactonization.
67. This type of building block has been obtained (1) from the chiral pool:
68. a) T. Ibuka, M. Tanake, S. Nishii, Y Yamamoto, J. Am. Chem. Soc. 1989, 111, 4864-4872;
69. b) Y Petit, C. Sanner, M. Larchevêque, Tetrahedron Lett. 1990, 31, 2149-2152;
70. c) B. X Martin, X M. Clough, G. Pattenden, LR. Waldron, Tetrahedron Lett. 1993, 34, 5151-5154;
71. d) X M. Clough, H. Dube, B. X Martin, G. Pattenden, K. S. Reddy, I. R. Waldon, Org. Biomol. Chem. 2006, 4, 2906-2911; (2) using a chiral auxiliary:
72. e) Y Honda, A. Ori, G.-i. Tsuchihashi, Chem. Lett. 1986, 13-16;
73. using asymmetric photodeconjugation in up to 91% ee: f) O. Piva, R. Mortezaei, F. Henin, J. Muzart, X-P Pete, J. Am. Chem. Soc. 1990, 112, 9263-9272;
74. g) O. Piva, X-P. Pete, Tetrahedron Lett. 1990, 31, 5157-5160.
75. a) S. H. Hong, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2004, 126, 7414-7415;
76. b) R. Raju, L. X Allen, T. Le, CD. Taylor, A. R. Howell, Org. Lett. 2007, 9, 1699-1701.
77. This type of building block has been obtained (1) by asymmetric hydrogenation in a)up to 90% ee: D.J. Ager, S. Babler, D. E. Froen, S. A. Laneman, D. P. Pantaleone, I. Prakash, B. Zhi, Org. Process Res. Dev. 2003, 7, 369-378;
78. b)up to 96% ee: X. Cheng, Q. Zhang, X-H. Xie, L.-X. Wang, Q.-L. Zhou, Angew. Chem. 2005, 111, 1142-1145;
79. Angew. Chem. Int. Ed. 2005, 44, 1118-1121;
80. c) up to 98% ee: X. Cheng, X.-H. Xie, S. Li, Q.-L. Zhou, Adv. Synth. Catal. 2006, 348, 1271-1276;
81. d) up to 97% ee: ref.[9e]; e)up to 93% ee: V. Moberg, M. Haukka, I. O. Koshevoy, R. Ortiz, E. Nordlander, Organometallics 2007, 26, 4090-4093;
82. f) up to 99% ee: S. Li, S.-F. Zhu, C-M. Zhang, S. Song, Q.-L. Zhou, J. Am. Chem. Soc. 2008, 130, 8584-8585;
83. enzymatically: g) K. Miyamoto, H. Ohta, J. Am. Chem. Soc. 1990, 112, 4077-4078;
84. h) B. Westermann, B. Krebs, Org. Lett. 2001, 3, 189-191;
85. i) R. Morrone, M. Piattelli, G. Nicolosi, Eur. J. Org. Chem. 2001, 1441-1443;
86. j) P. Beier, D. O'Hagan, Chem. Commun. 2002, 1680-1681;
87. k) L. M. Hutchins, L. Hunter, N. Ehya, M. D. Gibbs, P. L. Bergquist, C. A. Hutton, Tetrahedron: Asymmetry 2004, 15, 2975-2980;
88. E. Hedenström, H. Edlund, A.-B. Wassgren, G. Bergström, O. Anderbrant, F. Östrand, A. Sierpinski, M.-A. AugerRozenberg, A. Herz, W. Heitland, M. Varama, J. Chem. Ecol. 2006, 32, 2525-2541;
89. m) S. Sabbani, E. Hedenström, O. Nordin, J. Mol. Catal. B: Enzym. 2006, 42, 1-9; (3) via DKR:
90. n) X Norinder, K. Bogar, L. Kanupp, J.-E. Bäckvall, Org. Lett. 2007, 9, 5095-5098; (4) using a chiral auxiliary; for example:
91. o)A. G. Myers, B. H. Yang, H. Chen, L. McKinstry, D. J. Kopecky;, J. L. Gleason, J. Am. Chem. Soc. 1997, 119, 6496-6511.
92. R. W Ficken, M. S. Ficken, J. P. Hailman, Science 1974, 183, 760-763.
93. X Guiard, A. Collmann, M. Gilleron, L. Mori, G. De Libero, X Prandi, G. Puzo, Angew. Chem. 2008, 120, 9880-9884;
94. Angew. Chem. Int. Ed. 2008, 47, 9734-9738.
95. M. Arai, T. Kawasuji, E. Nakamura, J. Org. Chem. 1993, 55, 5121-5129.
96. This kind of building block has been obtained (1) using chiral auxiliaries:
97. a) W. Oppolzer, A.J. Kingma, G. Poli, Tetrahedron 1989, 45, 479-488;
98. b) S. ItO, T. Tsunoda, Pure Appl. Chem. 1990, 62, 1405-1408;
99. c) E. J. Corey, D.-H. Lee, J. Am. Chem. Soc. 1991, 113, 4026-4028;
100. d) T. Tsunoda, M. Sakai, O. Sasaki, Y Sako, Y Hondo, S. It, Tetrahedron Lett. 1992, 33, 1651-1654; (2) via enantioselective Claisen rearrangement in up to 95% ee:
101. e) P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
102. This kind of cyclic building block has been obtained (1) enzymatically:
103. a) H. Akita, H. Matsukura, T. Oishi, Chem. Pharm. Bull. 1986, 34, 2656-2659;
104. b) D. Buisson, S. Henrot, M. Larchevêque, R. Azerad, Tetrahedron Lett. 1987, 28, 5033-5036; (2) from the chiral pool;
105. c) M. Larchevêque, S. Henrot, Tetrahedron 1987, 43, 2303-2310;
106. d)Y Hamada, F. Yokokawa, M. Kabeya, K. Hatano, Y Kurono, T. Shioiri, Tetrahedron 1996, 52, 8297-8306.
107. M. H. Junttila. O. O. E. Hormi, J. Org. Chem. 2009, 74, 3038-3047.
108. The observed enantioselectivities in this reaction are representative for terminal olefins.
109. a) J. Schuppan, H. Wehlan, S. Keiper, U. Koert, Angew. Chem. 2001, 113, 2125-2128;
110. Angew. Chem. Int. Ed. 2001, 40, 2063-2066;
111. b) J. Schuppan, H. Wehlan, S. Keiper, U. Koert, Chem. Eur. J. 2006, 12, 7364-7377.
112. X Barluenga, M. Alvarez-Pérez, F. Rodriguez, F. X Fañanás, X A. Cuesta, S. Garcia-Granda, J. Org. Chem. 2003, 65, 6583-6586.
113. According to the literature, the 5-membered lactone products possess the all-trans configuration: J.-M. Garnier, S. Robin, R. Guillot, G. Rousseau, Tetrahedron: Asymmetry 2007, 75, 1434-1442. In NOESY-NMR experiments for 19 [(3R,4S')-4-iodo-3-methyldihydrofuran-2(3//)-one] we found a stronger coupling between one of C5 protons and the C4 proton and a weaker coupling with the other C5 proton and the C4 proton. The weaker coupling is as strong as the coupling of the protons of C4 and C3. For 22 [(3R,4S,5R)-5-hexyl-4iodo-3- methyldihydrofuran-2(377)-one] we found a weak coupling between the protons of C5 and C4 and a coupling similar in strength for the C4 and C3 protons. In combination with the expected irans-conformation for the protons of C4 and C5 arising from inti-addition of the carboxylate on the iodonium intermediate this most likely indicates an all-trans conformation of both 19 and 22.
114. The bromo substituted 4-membered lactone can also be synthesized:
115. a) I. Shibata, M. Toyota, A. Baba, H. Matsuda, Chem. Express 1989, 4, 241-244;
116. b) S. R. Mellegaard, X A. Tunge, J. Org. Chem. 2004, 69, 8979-8981.
117. D. Fischer, H. Tomeba, N. K. Pahadi, N.T. Patil, Z. Huo, Y Yamamoto, J. Am. Chem. Soc. 2008, 130, 15720-15725.
118. N2 attack of the carboxylate on the terminal iodoalkane.
119. E. X Corey, T. Hase, Tetrahedron Lett. 1979, 335-338.
120. a) P. A. Grieco, Y S. Hon, A. Perez-Medrano, J. Am. Chem. Soc. 1988, 110, 1630-1631;
121. b)K. S. Chu, G. R. Negrete, J. P. Konopelski, J. Org. Chem. 1991, 56, 5196-5202.
122. 2 used for the work-up of this reaction.
123. This procedure was based on a procedure described in: S. Liu, R. P. Hanzlik J. Med. Chem. 1992, 35, 1067-1075.
124. G. Sun, P.S. Savle, R. D. Gandour, N.N. a'Bhaírd, R. R. Ramsay, F. R. Fronczek, J. Org. Chem. 1995, 60, 6688-6695.
125. A. W. van Zijl, A. X Minnaard, B. L. Feringa, J. Org. Chem. 2008, 73, 5651-5653.
126. R. Álvarez-García, J. M. Torres-Valencia, L. U. Román, X D. Hernández, C. M. Cerda-García-Rojas, P. JosephNathan, Phytochemistry 2005, 66, 639-642.
127. K. Yoshinaga, T. Krro, K. Ohkubo, Bull. Chem. Soc. Jpn. 1983, 56, 1786-1790.
128. P. R. Andreana, J. S. McLellan, Y Chen, P. G. Wang, Org. Lett. 2002, 4, 3875-3878.
129. M. H. Rabinowitz, R. C Andrews, J. D. Becherer, D. M. Bickett, D. G. Bubacz, J. G. Conway, D. J. Cowan, M. Gaul, K. Glennon, M. H. Lambert, M. A. Leesnitzer, D. L. McDougald, M. L. Moss, D. L. Musso, M. C Rizzolio, J. Med. Chem. 2001, 44, 4252-4267.
130. I. C Stewart, C. J. Douglas, R. H. Grubbs, Org. Lett. 2008,70,441-444.
131. Occasionaly the product was polluted with 2,6dichlorobenzoquinone, in these cases a yellow oil was obtained.
132. H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447-449;
133. Angew. Chem. Int. Ed Engl. 1996, 35, 448451.
134. T. Řexanka, R. Dvořáková, L. O. Hanuš, V. M. Debitsky, Eur. J. Org. Chem. 2004, 995-1001.
135. I. Shibata, F. Matsuo, A. Baba, H. Matsuda, J. Org. Chem. 1991, 56, 475-476.
136. G. Rajendra, M.J. Miller, J. Org. Chem. 1987, 52, 4471-4477.