Principles and Applications of Asymmetric Synthesis

8.6 REFERENCES 503

M.S.; Newton, R. F.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Chem. Commun. 1990, 619. (n) Hudlicky, T.; Price, J. D. Synlett. 1990, 159.

24.(a) Suga, T.; Hamada, H.; Hirata, T. Chem. Lett. 1987, 471. (b) Hamada, H. Bull. Chem. Soc. Jpn. 1988, 61, 869.

25.Akakabe, Y.; Takahashi, M.; Kamezawa, M.; Kikuchi, K.; Tachibana, H.; Ohtani, T.; Naoshima, Y. J. Chem. Soc. Perkin Trans. 1 1995, 1295.

26.Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301.

27.Uozumi, T.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.

28.Uozumi, Y.; Lee, S.; Hayashi, T. Tetradedron Lett. 1992, 33, 7185.

29.Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.

30.(a) Bode, B. M.; Day, P. N.; Gordon, M. S. J. Am. Chem. Soc. 1998, 120, 1552.

(b) Maruyama, Y.; Yamamura, K.; Nakayama, I.; Yoshiuchi, K.; Ozawa, F.

J.Am. Chem. Soc. 1998, 120, 1421.

31.For reviews: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. Int. Ed. Engl. 1990, 29, 977. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.

(c) Rosini, C.; Franzini, L.; Ra¨aelli, A.; Salvadori, P. Synthesis 1992, 503.

32.Govindachari, T. R.; Nagarajan, K.; Parthasarathy, P. C.; Rajagopalan, T. G.; Desai, H. K.; Kartha, G.; Chen, S. L.; Nakanishi, K. J. Chem. Soc. Perkin Trans. 1 1974, 1413.

33.(a) Huang, L.; Si, Y.; Snatzeke, G.; Zheng, D.; Zhou, J. Collect. Czech. Chem. Commun. 1988, 53, 2664. (b) Recent synthesis: Meyers, A. I.; Willemsen, J. J.

Tetrahedron 1998, 54, 10493.

34.(a) Uchida, I.; Ezaki, M.; Shigematsu, N.; Hashimoto, M. J. Org. Chem. 1985, 50, 1341. (b) Kannan, R.; Williams, D. H. J. Org. Chem. 1987, 52, 5435.

35.Tomioka, K.; Ishiguro, T.; Koga, K. Tetrahedron Lett. 1980, 23, 2973.

36.Cram, D. J.; Cram, J. M. Science (Washington D. C.) 1974, 183, 803.

37.Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.

38.Moorlag, H.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 6989.

39.Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.

40.Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869.

41.Meyers, A. I.; Nguyen, T. H. Tetrahedron Lett. 1995, 36, 5873.

42.Lipshuz, B. H.; Liu, Z.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567.

43.Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1958, 81, 5819.

44.Andrus, M. B.; Argade, A. B.; Chen, X.; Pammet, M. G. Tetrahedron Lett. 1995, 36, 2945.

45.DattaGupta, A.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633.

46.Bolm, C.; Schlinglo¨, G.; Weickhardt, K. Angew. Chem. Int. Ed. Engl. 1994, 33, 1848.

47.Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369.

48.(a) Denmark, S. E.; Chen, C. J. Am. Chem. Soc. 1992, 114, 10674. (b) Denmark,

S.E.; Rivera, I. J. Org. Chem. 1994, 59, 6887.

49.Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446.

504ENZYMATIC REACTIONS AND MISCELLANEOUS ASYMMETRIC SYNTHESES

50.Tanaka, K.; Watanabe, T.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1997, 38, 8943.

51.Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.

52.GuetteÂ, M.; Capillon, J.; GuetteÂ, J. Tetrahedron 1973, 29, 3659.

53.(a) Soai, K.; Kawase, Y. Tetrahedron Asymmetry 1991, 2, 781. (b) Soai, K.; Hirose, Y.; Sakata, S. Tetrahedron Asymmetry 1992, 3, 677. (c) Soai, K.; Oshio, A.; Saito,

T.J. Chem. Soc. Chem. Commun. 1993, 811.

54.Pini, D.; Mastantuono, A.; Salvadori, P. Tetradedron Asymmetry 1994, 5, 1875.

55.Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T. K. Tetrahedron Asymmetry 1995, 6, 2641.

56.For a review, see Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.

57.Fukuzawa, S.; Tatsuzawa, M.; Hirano, K. Tetrahedron Lett. 1998, 39, 6899.

58.Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.

59.For reviews, see Tsuji, J. Palladium Reagents and Catalysts, John Willey & Sons, Chichester, 1995, pp 19±124.

60.(a) For explanation of the mechanism, see Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T. Organometallics 1993, 12, 4188. For catalytic asymmetric arylation of cyclic ole®ns, see (b) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421. (c) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. For other examples of asymmetric Heck reactions, see (d) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. (e) Kagechika, K.; Shibasaki, M.

J.Org. Chem. 1991, 56, 4093. (f ) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. (g) Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571.

61.Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846.

62.Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485.

63.Ozawa, F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505.

64.Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115.

65.(a) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. (b) Zhu, G.; Lu, X. Tetradedron Asymmetry 1995, 6, 885.

66.(a) Newman, M. S.; Magerlein, B. J. Org. React. 1945, 5, 413. (b) Ballester, M.

Chem. Rev. 1955, 55, 283.

67.Annunziata, R.; Ban®, S.; Colonna, S. Tetrahedron Lett. 1985, 26, 2471.

68.Ohkata, K.; Kimura, J.; Shinohara, Y.; Takagi, R.; Hiraga, Y. J. Chem. Soc. Chem. Commun. 1996, 2411.

ÂÂ

69.Bako, P.; SzoÈllosy, A.; Bombicz, P.; ToÈke, L. Synlett 1997, 291.

70.Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.

71.(a) Villacorta, G. M.; Rao, C. P.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 3175.

(b) Ahn, K. H.; Klassen, R. B.; Lippard, S. J. Organometallics 1990, 9, 3178.

72.De Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374.

73.(a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; De Vries, A. H. M. Angew. Chem. Int. Ed. Engl. 1997, 36, 2620. (b) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104.

8.6 REFERENCES 505

74.(a) Yan, M.; Yang, L.; Wong, K.; Chan, A. S. C. J. Chem. Soc. Chem. Commun. 1999, 11. (b) Yan, M.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 6645.

75.Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994.

76.Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.

77.Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.

78.Gomez-Bengoa, E.; Heron, N. M.; Didiuk, M. T.; Luchaco, C. A.; Hoveyda, A. H.

J.Am. Chem. Soc. 1998, 120, 7649.

79.(a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (b) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.

80.(a) Krause, N.; Gerold, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 187. (b) Krause,

N.Angew. Chem. Int. Ed. Engl. 1998, 37, 283.

81.KoÈnig, K. E.; Bachman, G. L.; Vineyard, B. D. J. Org. Chem. 1980, 45, 2362.

82.(a) Roucoux, A.; Devocelle, M.; Carpentier, J.; Agbossou, F.; Mortreux, A. Synlett 1995, 358. (b) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.

(c) Mashima, K.; Akutagawa, T.; Zhang, X.; Takaya, H.; Taketomi, T.; Kumobayashi, H.; Akutagawa, S. J. Organomet. Chem. 1992, 428, 213.

83.(a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653.

(b) Burk, M. J.; Harlow, R. L. Angew. Chem. Int. Ed. Eng. 1990, 29, 1462. (c) Burk,

M.J.; Feaster, J. E.; Harlow, R. L. Tetradedron Asymmetry 1991, 2, 569.

84.Saburi, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877.

85.(a) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611. (b) Corey, E. J.; Cheng, X.; Cimprich, K. A.; Sarshar, S. Tetrahedron Lett. 1991, 32, 6835.

86.Braun, M.; von Der Hagen, A.; WaldmuÈller, D. Liebigs Ann. Chem. 1995, 1447.

87.(a) Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393. (b) Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984. (c) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.

88.Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35, 3137.

89.Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 2768.

90.For the terminology of desymmetrization, see Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566.

91.Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738.

92.Mislow K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, 3319.

93.(a) Trost, B. M.; van Vranken, D, L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (b) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.

(c) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (d) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037. (e) Trost, B. M.; Madsen, R.; Guile,

S.D. Tetrahedron Lett. 1997, 38, 1707.

94.Trost, B. M.; Patterson, D. E. J. Org. Chem. 1998, 63, 1339.

95.Miyafuji, A.; Katsuki, T. Tetrahedron 1998, 54, 10339.

96.(a) StraÈter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2024. (b) Wilcox, D. E. Chem. Rev. 1996, 96, 2435. (c) Steinhagen, H.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 2339.

506ENZYMATIC REACTIONS AND MISCELLANEOUS ASYMMETRIC SYNTHESES

97.(a) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M.

J.Org. Chem. 1995, 60, 7388. (b) Sasai, H.; Yamada, Y. M. A.; Suzuki, T.; Shibasaki, M. Tetrahedron 1994, 50, 12313. (c) Sasai, H.; Kim, W.; Suzaki, T.; Shibasaki, M.; Mitusda, M.; Hasegawa, J.; Ohashi, T. Tetrahedron Lett. 1994, 35, 6123. (d) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. (e) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372. (f ) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571. (g) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.

(h) Sasai, H.; Arai, S. Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.

(i) Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926. ( j) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104. (k) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.

98.Van Koten, G. Pure Appl. Chem. 1994, 66, 1455.

99.Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168.

100.Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641.

101.Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780.

102.Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924.

103.For a review, see Avalos, M.; Babiano, R.; Cintas, P.; Jimemez, J. L.; Palacios,

J.C. Tetradedron Asymmetry 1997, 8, 2997.

104.Puchot, C.; Samuel, O.; DunÄach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.

105.These reactions include (1) addition of organozincs to aldehydes: (a) Noyori, R. Chem. Soc. Rev. 1989, 18, 187. (2) 1,4-Addition of organozinc compounds:

(b) Bolm, C. Tetradedron Asymmetry 1991, 2, 701. (c) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (d) Bolm, C.; Felder, M.; MuÈller, J. Synlett 1992, 439. (3) Asymmetric glyoxylate-ene reaction: (e) Terada, M.; Mikami, K.; Nakai, T. J. Chem. Soc. Chem. Commum. 1990, 1623. (4) Trimethylsilylcyanation of carbonyl compounds: (f ) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc. Chem. Commun. 1990, 1364. (5) Allylation and aldol condensation on aldehydes:

(g) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (h) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (6) Asymmetric epoxidation: (i) Guillaneux, D.; Zhao, S. H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430.

(7) Asymmetric ring-opening of meso-epoxides: ( j) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924. (8) Diels-Alder reaction, hetero-Diels-Alder reaction and 1,3-dipolar cycloaddition reaction: (k) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; KuÈhnle F. N. M.

J.Org. Chem. 1995, 60, 1788.

106.Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.

107.(a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028. (b) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.

8.6 REFERENCES 507

108.Girard, C.; Kagan, H. B. Angew. Chem. Int. Ed. Engl. 1998, 37, 2922.

109.Faller, J. W.; Parr, J. J. Am. Chem. Soc. 1993, 115, 804.

110.Faller, J. W.; Tokunaga, M. Tetrahedron Lett. 1993, 34, 7359.

111.Mikami, K.; Matsukawa, S. Nature 1997, 385, 613.

112.Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R.

Angew. Chem. Int. Ed. Engl. 1999, 38, 495.

113.Reetz, M. T.; Neugebauer, T. Angew. Chem. Int. Ed. Engl. 1999, 38, 179.

114.(a) Matsuda, Y.; Kaneko, T.; Oguni, N. J. Am. Chem. Soc. 1988, 110, 7877. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.

115.(a) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (b) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (c) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K., Tetradedron Asymmetry 1997, 8, 1717.

116.Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem. Int. Ed. Engl. 1999, 38, 659.

117.Moradpour, A.; Nicoud, J. F.; Balavoine, G.; Kagan, H. B.; Tsoucaris, G. J. Am. Chem. Soc. 1971, 93, 2353.

118.(a) Bernstein, W. J.; Calvin, M.; Buchardt, O. J. Am. Chem. Soc. 1972, 94, 494.

(b) Bernstein, W. J.; Calvin, M.; Buchardt, O. J. Am. Chem. Soc. 1973, 95, 527.

119.Flores, J. J.; Bonner, W. A.; Massey, G. A. J. Am. Chem. Soc. 1977, 99, 3622.

120.Shibata, T.; Yamamoto, J.; Matsumoto, N.; Yonekubo, S.; Osanai, S.; Soai, K.

J. Am. Chem. Soc. 1998, 120, 12157.