SCOPUS 정보 검색 플랫폼

ACS Symposium Series

Volumn 639, Issue , 1996, Pages 73-82

Asymmetric Synthesis of Functionalized Fluorinated Cyclopropanes and Its Application to Fluoromethano Amino Acids

(3) Taguchi, Takeo a Shibuya, Akira a Morikawa, Tsutomu a

a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842473809 PISSN: 00976156 EISSN: None Source Type: Book Series
DOI: 10.1021/bk-1996-0639.ch005 Document Type: Article

Times cited : (1)

References (51)

1
- 0003352699
- Biochemistry of the Cyclopropyl Group
- Patai, S.; Rappoport, Z., Eds.; Wiley, New York, Chapter 16
- (a) Lin, H. W.; Walsh, C. T. Biochemistry of the Cyclopropyl Group; In 'The Chemistry of the Cyclopropyl Group'; Patai, S.; Rappoport, Z., Eds.; Wiley, New York, 1987; Chapter 16.
- (1987) The Chemistry of the Cyclopropyl Group
- Lin, H.W.¹ Walsh, C.T.²

2
- 84990162459
- (b) Suckling, C. J. Angew. Chem. Int. Ed. Engl. 1988, 27, 537-552.
- (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 537-552
- Suckling, C.J.¹

3
- 15644378136
- (c) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Takano, J. Chem. Rev. 1989, 89, 165-198.
- (1989) Chem. Rev. , vol.89 , pp. 165-198
- Wong, H.N.C.¹ Hon, M.-Y.² Tse, C.-W.³ Yip, Y.-C.⁴ Takano, J.⁵

4
- 2142690327
- (d) Salaun, J. Chem. Rev. 1989, 89, 1247-1270.
- (1989) Chem. Rev. , vol.89 , pp. 1247-1270
- Salaun, J.¹

5
- 0025074114
- (a) Stammer, C. H. Tetrahedron 1990, 46, 2231-2254.
- (1990) Tetrahedron , vol.46 , pp. 2231-2254
- Stammer, C.H.¹

6
- 0023162457
- (b) Shimohigashi, Y.; Costa, T.; Pfeiffer, A.; Herz, A.; Kimura, H.; Stammer C. H. FEBS Lett. 1987, 222, 71-74.
- (1987) FEBS Lett. , vol.222 , pp. 71-74
- Shimohigashi, Y.¹ Costa, T.² Pfeiffer, A.³ Herz, A.⁴ Kimura, H.⁵ Stammer, C.H.⁶

7
- 0003571014
- (c) Pirrug, M. C.; Dunlup, S. E.; Trinks, U. P. Helv. Chim. Acta 1989, 1301-1310.
- (1989) Helv. Chim. Acta , pp. 1301-1310
- Pirrug, M.C.¹ Dunlup, S.E.² Trinks, U.P.³

8
- 0026439341
- d) Burgess, K.; Ho, K.-K. J. Org. Chem. 1992, 57, 5931-5936.
- (1992) J. Org. Chem. , vol.57 , pp. 5931-5936
- Burgess, K.¹ Ho, K.-K.²

9
- 0001296375
- (e) Burgess, K.; Ho, K.-K. Pettitt, B. M. J. Am. Chem. Soc. 1994, 116, 799-800.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 799-800
- Burgess, K.¹ Ho, K.-K.² Pettitt, B.M.³

10
- 0028383384
- (f) Kodama, H.; Shimohigashi, Y. J. Syn. Org. Chem. Jpn. 1994, 52, 180-191.
- (1994) J. Syn. Org. Chem. Jpn. , vol.52 , pp. 180-191
- Kodama, H.¹ Shimohigashi, Y.²

11
- 0026659675
- Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh T.; Nakatani, K.; Hayata, I.; Akiba, T.; Terashima, S. Tetrahedron Lett. 1992, 33, 3483-5486 and 3487-3490.
- (1992) Tetrahedron Lett. , vol.33 , pp. 3483-5486
- Tamura, O.¹ Hashimoto, M.² Kobayashi, Y.³ Katoh, T.⁴ Nakatani, K.⁵ Hayata, I.⁶ Akiba, T.⁷ Terashima, S.⁸

12
- 0019152583
- (a) Paech, C.; Salach, J. L.; Singer, T. P.; J. Biol. Chem. 1980, 255, 2700-1704.
- (1980) J. Biol. Chem. , vol.255 , pp. 2700-11704
- Paech, C.¹ Salach, J.L.² Singer, T.P.³

13
- 0042454692
- b) Silvermann, R. B.; Hoffmann, S. J.; Catus, II, W. B. J. Am. Chem. Soc. 1980, 102, 7120-7128.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7120-7128
- Silvermann, R.B.¹ Hoffmann, S.J.² Catus II, W.B.³

14
- 0001717886
- (c) MacDonald, T. L.; Zirvi, K.; Burka, L. T.; Peyman, P.; Guengrich, F. P. J. Am. Chem. Soc. 1982, 104, 2050-2052.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 2050-2052
- MacDonald, T.L.¹ Zirvi, K.² Burka, L.T.³ Peyman, P.⁴ Guengrich, F.P.⁵

15
- 0023875531
- (a) Yamanoi, K.; Ohfune, Y.; Watanabe, K.; Li, P.-N.; Takeuchi, H. Tetrahedron Lett. 1988, 29, 1181-1184.
- (1988) Tetrahedron Lett. , vol.29 , pp. 1181-1184
- Yamanoi, K.¹ Ohfune, Y.² Watanabe, K.³ Li, P.-N.⁴ Takeuchi, H.⁵

16
- 0025797354
- (b) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167-4176.
- (1991) J. Org. Chem. , vol.56 , pp. 4167-4176
- Shimamoto, K.¹ Ishida, M.² Shinozaki, H.³ Ohfune, Y.⁴

17
- 0027244355
- (c) Raghavan, S.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Tetrahedron Lett. 1993, 34, 5765-5768.
- (1993) Tetrahedron Lett. , vol.34 , pp. 5765-5768
- Raghavan, S.¹ Ishida, M.² Shinozaki, H.³ Nakanishi, K.⁴ Ohfune, Y.⁵

18
- 0025023564
- (d) Pellicciari, R.; Natalini, B.; Marinizzi, M.; Monahan, J. B.; Snyder, J. P. Tetrahedron Lett. 1990, 31, 139-142.
- (1990) Tetrahedron Lett. , vol.31 , pp. 139-142
- Pellicciari, R.¹ Natalini, B.² Marinizzi, M.³ Monahan, J.B.⁴ Snyder, J.P.⁵

19
- 0024495582
- (a) Shinozaki, H.; Ishida, M.; Shimamoto, K.; Ohfune, Y. Brain Res. 1989, 480, 355-359.
- (1989) Brain Res. , vol.480 , pp. 355-359
- Shinozaki, H.¹ Ishida, M.² Shimamoto, K.³ Ohfune, Y.⁴

20
- 0024843541
- (b) Shinozaki, H.; Ishida, M.; Shimamoto, K.; Ohfune, Y. Br. J. Pharmacol. 1989, 98, 1213-1224.
- (1989) Br. J. Pharmacol. , vol.98 , pp. 1213-1224
- Shinozaki, H.¹ Ishida, M.² Shimamoto, K.³ Ohfune, Y.⁴

21
- 0026503073
- (c) Kawai, M.; Horikawa, Y.; Ishihara, T.; Shimamoto, K.; Ohfune, Y. Eur. J. Pharmac. 1992, 211, 195-202.
- (1992) Eur. J. Pharmac. , vol.211 , pp. 195-202
- Kawai, M.¹ Horikawa, Y.² Ishihara, T.³ Shimamoto, K.⁴ Ohfune, Y.⁵

22
- 0023237559
- (a) Welch, J. T. Tetrahedron 1987, 43, 3123-3197.
- (1987) Tetrahedron , vol.43 , pp. 3123-3197
- Welch, J.T.¹

23
- 0000465570
- Fluorine-Substituted Neuroactive Amines
- Welch, J. T. Ed.; ACS Symposium Series 456, Washington DC
- (b) Kirk, K. L. "Fluorine-Substituted Neuroactive Amines". In 'Selective Fluonnation in Organic and Bioorganic Chemistry'; Welch, J. T. Ed.; ACS Symposium Series 456, Washington DC, 1991; pp136-155.
- (1991) Selective Fluonnation in Organic and Bioorganic Chemistry , pp. 136-155
- Kirk, K.L.¹

24
- 0001773492
- (a) Simmons, H. E.; Cairns, T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. 1973, 20, 1-131.
- (1973) Org. React. , vol.20 , pp. 1-131
- Simmons, H.E.¹ Cairns, T.L.² Vladuchick, S.A.³ Hoiness, C.M.⁴

25
- 0002664878
- (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53-58.
- (1968) Tetrahedron , vol.24 , pp. 53-58
- Furukawa, J.¹ Kawabata, N.² Nishimura, J.³

26
- 0000522532
- (a) Poulter, C. D.; Friedrich, E. C.; Winstein S. J. Am. Chem Soc. 1969, 91, 6892-6894.
- (1969) J. Am. Chem Soc. , vol.91 , pp. 6892-6894
- Poulter, C.D.¹ Friedrich, E.C.² Winstein, S.³

27
- 0000243233
- (b) Molander, G. A.; Harring, L. S. J. Org Chem. 1989, 54, 3525-3532.
- (1989) J. Org Chem. , vol.54 , pp. 3525-3532
- Molander, G.A.¹ Harring, L.S.²

28
- 0001701454
- (c) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723-725.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 723-725
- Denmark, S.E.¹ Edwards, J.P.² Wilson, S.R.³

29
- 0027058320
- Morikawa, T.; Sasaki, H.; Mon, K.; Shiro, M.; Taguchi, T. Chem. Pharm. Bull. 1992, 40, 3189-3193.
- (1992) Chem. Pharm. Bull. , vol.40 , pp. 3189-3193
- Morikawa, T.¹ Sasaki, H.² Mon, K.³ Shiro, M.⁴ Taguchi, T.⁵

30
- 0010980241
- For recent examples of asymmetric Simmons-Smith reactions: (a) Mon, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447-6458. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. (c) Frutos, M. P.; Fernandez, M. D.; Alvarez, E. F.; Bernarbe, M. Tetrahedron Lett. 1991, 32, 541-542. (d) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61-64. (g) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
- (1986) Tetrahedron , vol.42 , pp. 6447-6458
- Mon, A.¹ Arai, I.² Yamamoto, H.³

31
- 0000465485
- For recent examples of asymmetric Simmons-Smith reactions: (a) Mon, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447-6458. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. (c) Frutos, M. P.; Fernandez, M. D.; Alvarez, E. F.; Bernarbe, M. Tetrahedron Lett. 1991, 32, 541-542. (d) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61-64. (g) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
- (1989) J. Org. Chem. , vol.54 , pp. 250-253
- Mash, E.A.¹ Torok, D.S.²

32
- 0025959930
- For recent examples of asymmetric Simmons-Smith reactions: (a) Mon, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447-6458. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. (c) Frutos, M. P.; Fernandez, M. D.; Alvarez, E. F.; Bernarbe, M. Tetrahedron Lett. 1991, 32, 541-542. (d) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61-64. (g) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
- (1991) Tetrahedron Lett. , vol.32 , pp. 541-542
- Frutos, M.P.¹ Fernandez, M.D.² Alvarez, E.F.³ Bernarbe, M.⁴

33
- 0001553673
- For recent examples of asymmetric Simmons-Smith reactions: (a) Mon, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447-6458. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. (c) Frutos, M. P.; Fernandez, M. D.; Alvarez, E. F.; Bernarbe, M. Tetrahedron Lett. 1991, 32, 541-542. (d) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61-64. (g) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 8166-8167
- Charette, A.B.¹ Cote, B.² Marcoux, J.-F.³

34
- 0001881941
- For recent examples of asymmetric Simmons-Smith reactions: (a) Mon, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447-6458. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. (c) Frutos, M. P.; Fernandez, M. D.; Alvarez, E. F.; Bernarbe, M. Tetrahedron Lett. 1991, 32, 541-542. (d) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61-64. (g) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
- (1992) Chem. Lett. , pp. 61-64
- Ukaji, Y.¹ Nishimura, M.² Fujisawa, T.³

35
- 0026590430
- For recent examples of asymmetric Simmons-Smith reactions: (a) Mon, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447-6458. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. (c) Frutos, M. P.; Fernandez, M. D.; Alvarez, E. F.; Bernarbe, M. Tetrahedron Lett. 1991, 32, 541-542. (d) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61-64. (g) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575-2578.
- (1992) Tetrahedron Lett. , vol.33 , pp. 2575-2578
- Takahashi, H.¹ Yoshioka, M.² Ohno, M.³ Kobayashi, S.⁴

36
- 0028347971
- Morikawa, T.; Sasaki, H.; Hanai, R.; Shibuya, A.; Taguchi, T. J. Org. Chem. 1994, 59, 97-103.
- (1994) J. Org. Chem. , vol.59 , pp. 97-103
- Morikawa, T.¹ Sasaki, H.² Hanai, R.³ Shibuya, A.⁴ Taguchi, T.⁵

37
- 0011423161
- Tarant, P., Ed.; Marcell Dekker Inc.; New York
- (a) Burton, D. J.; Hahnfeld, J. C. Fluorine Chemistry Reviews; Tarant, P., Ed.; Marcell Dekker Inc.; New York, 1977, Vol 8, pp 153-179.
- (1977) Fluorine Chemistry Reviews , vol.8 , pp. 153-179
- Burton, D.J.¹ Hahnfeld, J.C.²

38
- 0010349739
- (b) Dolbier, Jr., W. R.; Wojtowicz, H.; Burkholder, C. R. J. Org. Chem. 1990, 55, 5420-5422.
- (1990) J. Org. Chem. , vol.55 , pp. 5420-5422
- Dolbier Jr., W.R.¹ Wojtowicz, H.² Burkholder, C.R.³

39
- 0027965577
- Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423-1426.
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1423-1426
- Taguchi, T.¹ Shibuya, A.² Sasaki, H.³ Endo, J.⁴ Morikawa, T.⁵ Shiro, M.⁶

40
- 0029655674
- Shibuya, A.; Kurishita, M.; Ago, C.; Taguchi, T. Tetrahedron 1996, 52, 271-278.
- (1996) Tetrahedron , vol.52 , pp. 271-278
- Shibuya, A.¹ Kurishita, M.² Ago, C.³ Taguchi, T.⁴

41
- 1842593730
- Honolulu, HI, USA, Dec. Abstract No. 666
- Taguchi, T.; Shibuya, A.; Kurishita, M. 1995 International Chemical Congress of Pacific Basin Societies; Honolulu, HI, USA, Dec. 1995. Abstract No. 666.
- (1995) 1995 International Chemical Congress of Pacific Basin Societies
- Taguchi, T.¹ Shibuya, A.² Kurishita, M.³

42
- 0025696335
- (a) Ishida, M.; Akagi, H.; Shimamoto, K.; Ohfune, Y.; Shinozaki, H. Brain Res. 1990, 537, 311-314.
- (1990) Brain Res. , vol.537 , pp. 311-314
- Ishida, M.¹ Akagi, H.² Shimamoto, K.³ Ohfune, Y.⁴ Shinozaki, H.⁵

43
- 0025079146
- (b) Nakagawa, Y.; Saito, K.; Ishihara, T.; Shinozaki, H.; Eur. J. Pharmac. 1990, 184, 205-206.
- (1990) Eur. J. Pharmac. , vol.184 , pp. 205-206
- Nakagawa, Y.¹ Saito, K.² Ishihara, T.³ Shinozaki, H.⁴

44
- 0026756866
- (c) Hayashi, Y.; Tanaka, Y.; Aramori, I.; Masu, M.; Shimamoto, K.; Ohfune, Y.; Nakanishi, S. Br. J. Pharmacol. 1992, 107, 539-543.
- (1992) Br. J. Pharmacol. , vol.107 , pp. 539-543
- Hayashi, Y.¹ Tanaka, Y.² Aramori, I.³ Masu, M.⁴ Shimamoto, K.⁵ Ohfune, Y.⁶ Nakanishi, S.⁷

45
- 0027493056
- (d) Lombardi, G.; Alesiami, M.; Leonardi, P.; Chericci, G.; Pellicciari, R.; Moroni, F. Br. J. Pharmacol. 1993, 110, 1407-1412.
- (1993) Br. J. Pharmacol. , vol.110 , pp. 1407-1412
- Lombardi, G.¹ Alesiami, M.² Leonardi, P.³ Chericci, G.⁴ Pellicciari, R.⁵ Moroni, F.⁶

46
- 0027676557
- (e) Costantino, G.; Natalini, B.; Pellicciari, R. ; Moroni, F.; Lombordi, G. Bioorg. Med. Chem. 1993, 1, 259-265.
- (1993) Bioorg. Med. Chem. , vol.1 , pp. 259-265
- Costantino, G.¹ Natalini, B.² Pellicciari, R.³ Moroni, F.⁴ Lombordi, G.⁵

47
- 0028328413
- Taguchi, T.; Sasaki, H.; Shibuya, A.; Morikawa, T. Tetrahedron Lett. 1994, 35, 913-916.
- (1994) Tetrahedron Lett. , vol.35 , pp. 913-916
- Taguchi, T.¹ Sasaki, H.² Shibuya, A.³ Morikawa, T.⁴

48
- 0001596458
- (a) Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162.
- (1989) Tetrahedron Lett. , vol.30 , pp. 3159-3162
- Takeyama, Y.¹ Ichinose, Y.² Oshima, K.³ Utimoto, K.⁴

49
- 0027410691
- (b) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 2169-2170.
- (1993) Tetrahedron Lett. , vol.34 , pp. 2169-2170
- Iseki, K.¹ Nagai, T.² Kobayashi, Y.³

50
- 0005521469
- (a) Prempee, P.; Radviroongit, S.; Thebtaranonth, Y. J. Org. Chem. 1983, 48, 3553-3556.
- (1983) J. Org. Chem. , vol.48 , pp. 3553-3556
- Prempee, P.¹ Radviroongit, S.² Thebtaranonth, Y.³

51
- 0000034861
- (b) Yamaguchi, M.; Tsukamoto, M.; Hirano, I. Tetrahedron Lett. 1985, 26, 1723-1726.
- (1985) Tetrahedron Lett. , vol.26 , pp. 1723-1726
- Yamaguchi, M.¹ Tsukamoto, M.² Hirano, I.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.