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Volumn , Issue 11, 2001, Pages 1719-1730

Efficient asymmetric synthesis of unnatural β-amino acids

(6) Bolm, C a Schiffers, I a Dinter, C L a Defrere L a Gerlach, A a Raabe, G a

a RWTH AACHEN UNIVERSITY (Germany)

Author keywords

Asymmetric ring opening; Chiral methyl esters; Curtius degradation; Enantiomer differentiating reaction; amino acids

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; DRUG PRODUCTS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS;

ESTERS;

ACID ANHYDRIDE; BETA AMINO ACID; CINCHONA ALKALOID; ESTER DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEGRADATION; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034846889 PISSN: 00397881 EISSN: None Source Type: Journal
DOI: 10.1055/s-2001-16745 Document Type: Article

Times cited : (65)

References (97)

1
- 0038688570
- Weinstein, B., Ed.; Marcel Dekker: New York
- (1977) Chemistry and Biochemistry of Amino Acids, Peptides and Proteins , vol.4 , pp. 242
- Drey, C.N.C.¹

2
- 0028130028
- (1994) Tetrahedron , vol.50 , pp. 9517
- Cole, D.C.¹

3
- 0028945772
- (1995) J. Org. Chem. , vol.60 , pp. 1177
- Matsunaga, S.¹ Fusetani, N.²

4
- 0003886739
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 1225
- Trimurtulu, G.¹ Ohtani, I.² Patterson, G.M.L.³ Moore, R.E.⁴ Corbett, T.H.⁵ Valeriote, F.A.⁶ Demchik, L.⁷

5
- 0017236348
- (1976) J. Antibiot. , vol.29 , pp. 97
- Umezawa, H.¹ Aoyagi, T.² Suda, H.³ Hamada, M.⁴ Takeuchi, T.⁵

6
- 0004030277
- Academic Press: New York
- (1982) Chemistry and Biology of β-Lactam Antibiotics
- Morin, R.B.¹ Gorman, M.²

7
- 0003822980
- Springer: Berlin
- (1990) Recent Progress in the Chemical Synthesis of Antibiotics and Related Natural Products
- Lukacs, G.¹ Ohno, M.²

8
- 0003821414
- (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 2135
- Georg, G.I.¹

9
- 0028341682
- (1994) J. Med. Chem. , vol.37 , pp. 1733
- Burnett, D.¹ Caplen, M.A.² Davis, H.R.³ Burrier, R.E.⁴ Clader, J.W.⁵

10
- 0029953285
- (1996) Helv. Chim. Acta , vol.79 , pp. 913
- Seebach, D.¹ Overhand, M.² Kühnle, F.N.M.³ Martinoni, B.⁴ Oberer, L.⁵ Hommel, U.⁶ Widmer, H.⁷

11
- 0030785114
- (1997) Chem. Commun. , pp. 2015
- Seebach, D.¹ Matthews, J.L.²

12
- 0345466641
- (1999) Helv. Chim. Acta , vol.82 , pp. 1539
- Abele, S.¹ Vögtli, K.² Seebach, D.³

13
- 0030461803
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 13071
- Appella, D.¹ Christianson, L.A.² Karle, I.L.³ Powell, D.R.⁴ Gellman, S.H.⁵

14
- 0030995823
- (1997) Nature , vol.387 , pp. 381
- Appella, D.¹ Christianson, L.A.² Klein, D.A.³ Powell, D.R.⁴ Huang, X.⁵ Barchi J., Jr.⁶ Gellman, S.H.⁷

15
- 0033532930
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6206
- Appella, D.¹ Christianson, L.A.² Katie, I.L.³ Powell, D.R.⁴ Gellman, S.H.⁵

16
- 0034728566
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2711
- Barchi J.J., Jr.¹ Huang, X.² Apella, D.H.³ Christianson, L.A.⁴ Durell, S.R.⁵ Gellman, S.H.⁶

17
- 0033518059
- (1999) Org. Lett. , vol.1 , pp. 1717
- Huck, B.R.¹ Langenhan, J.M.² Gellman, S.H.³

18
- 0033577324
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2309
- Appella, D.H.¹ Barchi J.J., Jr.² Durell, S.R.³ Gellman, S.H.⁴

19
- 0034679022
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4821
- Wang, X.¹ Espinosa, J.F.² Gellman, S.H.³

20
- 0003890215
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 3597
- Lee, H.-S.¹ LePlae, P.R.² Porter, E.A.³ Gellman, S.H.⁴

21
- 0542421525
- (1998) Acc. Chem. Res. , vol.31 , pp. 173
- Gellman, S.H.¹

22
- 0035804401
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 743
- Winkler, J.D.¹ Piatnitski, E.L.² Mehlmann, J.³ Kasparec, J.⁴ Axelsen, P.H.⁵

23
- 0000466569
- (1997) Chimia , vol.51 , pp. 244
- Hintermann, T.¹ Seebach, D.²

24
- 0000932043
- (1998) Chimia , vol.52 , pp. 734
- Seebach, D.¹ Abele, S.² Schreiber, J.V.³ Martinoni, B.⁴ Nussbaum, A.K.⁵ Schild, H.⁶ Schulz, H.⁷ Hennecke, H.⁸ Wössner, R.⁹ Bitsch, F.¹⁰

25
- 0032881267
- (1999) Helv. Chim. Acta , vol.82 , pp. 1774
- Werder, M.¹ Hauser, H.² Abele, S.³ Seebach, D.⁴

26
- 0033519190
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1223
- Gademann, K.¹ Ernst, M.² Hoyer, D.³ Seebach, D.⁴

27
- 0033949970
- (2000) Helv. Chim. Acta , vol.83 , pp. 16
- Gademann, K.¹ Ernst, M.² Seebach, D.³

28
- 17344384874
- (2000) Nature , vol.404 , pp. 565
- Porter, E.A.¹ Wang, X.² Lee, H.-S.³ Weisblum, B.⁴ Gellman, S.H.⁵

29
- 0033616105
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 12200
- Hamuro, Y.¹ Schneider, J.P.² De Grado, W.F.³

30
- 14844312173
- (1996) Chem. Soc. Rev. , pp. 117
- Cardillo, G.¹ Tomasini, C.²

31
- 0029906929
- (1996) Amino Acids , vol.11 , pp. 397
- Sewald, N.¹

32
- 0003693460
- Wiley-VCH: New York
- (1997) Enantioselective Synthesis of β-Amino Acids
- Juaristi, E.¹

33
- 0033986387
- (2000) Eur. J. Org. Chem. , pp. 1
- Abele, S.¹ Seebach, D.²

34
- 0001443660
- (1970) Helv. Chim. Acta , vol.53 , pp. 1057
- Penke, B.¹ Czombos, J.² Baláspiri, L.³ Petres, J.⁴ Kovács, K.⁵

35
- 13844272910
- (1995) Liebigs Ann. Chem. , pp. 1217
- Podlech, J.¹ Seebach, D.²

36
- 33748213822
- (1995) Angew. Chem., Int. Ed. Engl. , vol.3 , pp. 471
- Podlech, J.¹ Seebach, D.²

37
- 0032912088
- (1999) Synlett , pp. 195
- Bolm, C.¹ Gerlach, A.² Dinter, C.L.³

38
- 0034693091
- (2000) J. Org. Chem. , vol.65 , pp. 6984
- Bolm, C.¹ Schiffers, I.² Dinter, C.L.³ Gerlach, A.⁴

39
- 0033429252
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 3403
- Bernardi, A.¹ Arosio, D.² Dellavecchia, D.³ Micheli, F.⁴

40
- 0034644391
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 8793
- Stag, J.T.¹ Koch, G.² Carreira, E.M.³

41
- 0025170563
- (1990) Tetrahedron: Asymmetry , vol.1 , pp. 517
- Aitken, R.A.¹ Gopal, J.²

42
- 37049089874
- (1988) J. Chem Soc., Chem. Commun. , pp. 632
- Aitken, R.A.¹ Gopal, J.² Hirst, J.A.³

43
- 37049072812
- (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 1053
- Hiratake, J.¹ Inagaki, M.² Yamamoto, Y.³ Oda, J.⁴

44
- 37049097618
- (1985) J. Chem. Soc., Chem. Commun. , pp. 1717
- Hiratake, J.¹ Yamamoto, Y.² Oda, J.³

45
- 0034605437
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9542
- Chen, Y.¹ Tian, S.-K.² Deng, L.³

46
- 0035862637
- (2001) Tetrahedron Lett. , vol.42 , pp. 411
- Uozumi, Y.¹ Yasashima, K.² Miyachi, T.³ Nagai, S.-I.⁴

47
- 0000477646
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 175
- Willis, M.C.¹

48
- 0003610122
- Wiley-VCH: Weinheim
- (1999) Hydrolases in Organic Synthesis - Regio- and Stereoselective Biotransformations
- Bornscheuer, U.T.¹ Kazlauskas, R.J.²

49
- 0034622921
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 3569
- Martín-Vilà, M.¹ Muray, E.² Aguado, G.P.³ Alvarez-Larena, A.⁴ Branchadell, V.⁵ Minguillón, C.⁶ Giralt, E.⁷ Ortuño, R.M.⁸

50
- 0003887401
- note

51
- 0034725845
- (2000) J. Org. Chem. , vol.65 , pp. 4766
- Appella, D.H.¹ LePlae, P.R.² Raguse, T.L.³ Gellman, S.H.⁴

52
- 0141440727
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4291
- Martín-Vilà, M.¹ Minguillón, C.² Ortuño, R.M.³

53
- 0003886741
- note

54
- 20544433165
- (1964) J. Phys. Chem. , vol.68 , pp. 441
- Bondi, A.¹

55
- 33947320796
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 1199
- Allinger, N.L.¹ Hirsch, J.A.² Miller, M.A.³ Tyminski, I.J.⁴ Van-Catledge, F.⁵

56
- 0003932473
- ref. 15a

57
- 12044252424
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 6153
- Maruoka, K.¹ Akakura, M.² Saito, S.³ Ooi, T.⁴ Yamamoto, H.⁵

58
- 0028125319
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 9789
- Borzilleri, R.M.¹ Weinreb, S.M.²

59
- 0026337052
- (1991) Chem. Pharm. Bull. , vol.39 , pp. 2842
- Watanabe, F.¹ Matsuura, T.² Shirahase, K.³ Ohtani, M.⁴

60
- 84987162788
- (1993) Synlett , pp. 461
- Davies, S.G.¹ Ichihara, O.² Walters, I.A.S.³

61
- 37049076807
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1411
- Davies, S.G.¹ Ichihara, O.² Lenoir, I.³ Walters, I.A.S.⁴

62
- 0027327148
- (1993) Chem. Pharm. Bull. , vol.41 , pp. 1012
- Konosu, T.¹ Oida, S.²

63
- 0028024936
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1455
- Cimarelli, C.¹ Palmieri, G.²

64
- 0029773346
- (1996) J. Org. Chem. , vol.61 , pp. 5557
- Cimarelli, C.¹ Palmieri, G.²

65
- 0029934350
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1705
- Kanerva, L.T.¹ Csomós, P.² Sundholm, O.³ Bernáth, G.⁴ Fülöp, F.⁵

66
- 0029934597
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1789
- Csomós, P.¹ Kanerva, L.T.² Bernáth, G.³ Fülöp, F.⁴

67
- 0030561206
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 3565
- Theil, F.¹ Ballschuh, S.²

68
- 37049076053
- (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 2276
- Evans, C.¹ McCague, R.² Roberts, S.M.³ Sutherland, A.G.⁴ Wisdom, R.⁵

69
- 0003758769
- note

70
- 0032546515
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1249
- Harmat, N.J.S.¹ Di Bugno, C.² Criscuoli, M.³ Giorgi, R.⁴ Lippi, A.⁵ Martinelli, A.⁶ Monti, S.⁷ Subissi, A.⁸

71
- 0003824098
- Patent DE4443890A1
- (1996)
- Militzer, H.C.¹ Matzke, M.² Mittendorf, J.³ Schmidt, A.⁴ Ziegelbauer, K.⁵ Schoenfeld, W.⁶

72
- 0003907424
- 110180r
- (1996) Chem. Abstr. , vol.125

73
- 0003824769
- note

74
- 84955367639
- (1962) Chem. Ber. , vol.95 , pp. 1
- Weygand, F.¹ Hunger, K.²

75
- 0001356727
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 6333
- Patchornik, A.¹ Amir, B.² Woodward, R.B.³

76
- 0003760053
- (1986) J. Org. Chem. , vol.51 , pp. 1932
- Carpino, L.A.¹ Tunga, A.²

77
- 0027401721
- (1993) Tetrahedron , vol.49 , pp. 1985
- Canonne, P.¹ Akssira, M.² Dahdou, A.³ Kasmi, H.⁴ Boumzebra, M.⁵

78
- 84988112483
- (1993) Bull. Soc. Chim. Belg. , vol.102 , pp. 227
- Akssira, M.¹ Dahdou, A.² Kasmi, H.³

79
- 0003806686
- The failure of this reaction is in agreement with the observations by Gellman, see ref. 21

80
- 0028109561
- (1994) Tetrahedron Lett. , vol.35 , pp. 9169
- Pátek, M.¹ Drake, B.² Lebl, M.³

81
- 0030986896
- (1997) Tetrahedron , vol.53 , pp. 7539
- Seebach, D.¹ Jaeschke, G.² Gottwald, K.³ Matsuda, K.⁴ Formisano, R.⁵ Chaplin, D.A.⁶

82
- 0001678831
- (1998) J. Org. Chem. , vol.63 , pp. 1190
- Jaeschke, G.¹ Seebach, D.²

83
- 0000424872
- (1996) Helv. Chim. Acta , vol.79 , pp. 875
- Ramón, D.J.¹ Guillena, G.² Seebach, D.³

84
- 0004069938
- Kodansha Ltd.: Tokyo
- (1977) Stereo-Differentiating Reactions
- Izumi, Y.¹ Tai, A.²

85
- 0000679847
- (1996) Croat. Chem. Acta , vol.69 , pp. 669
- Kagan, H.B.¹

86
- 0000504871
- (1989) Tetrahedron Lett. , vol.30 , pp. 3663
- Alphand, V.¹ Archelas, A.² Furstoss, R.³

87
- 0027318206
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1341
- Petit, F.¹ Furstoss, R.²

88
- 37049075891
- (1995) J. Chem. Soc., Chem. Commun. , pp. 1247
- Bolm, C.¹ Schlingloff, G.²

89
- 0031562066
- (1997) Tetrahedron Lett. , vol.38 , pp. 989
- Back, T.G.¹ Nakajima, K.²

90
- 0001680511
- (1998) J. Org. Chem. , vol.63 , pp. 6566
- Back, T.G.¹ Nakajima, K.²

91
- 0003755408
- note

92
- 0003756293
- (1947) J. Am. Chem. Soc. , vol.69 , pp. 2313
- Frank, R.L.¹ Emmick, R.D.² Johnson, R.S.³

93
- 0003824101
- (1950) J. Am. Chem. Soc. , vol.72 , pp. 1648
- Craig, D.¹

94
- 0003754622
- Patent WO9803540A2, 1998
- Di Bugno, C.¹ Giorgi, R.² Harmat, N.³

95
- 0003828360
- 167714j
- (1998) Chem. Abstr. , vol.128

96
- 33751215153
- (1984) Tetrahedron Lett. , vol.25 , pp. 2557
- Kobayashi, S.¹ Kamiyama, K.² Iimori, T.³ Ohno, M.⁴

97
- 0025342356
- (1990) Chem. Pharm. Bull. , vol.38 , pp. 350
- Kobayashi, S.¹ Kamiyama, K.² Ohno, M.³

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