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Volumn 66, Issue 18, 2001, Pages 6046-6056

Conformational study and enantioselective, regiospecific syntheses of novel aminoxy trans-proline analogues derived from an acylnitroso Diels-Alder cycloaddition

(4) Shireman, B T a Miller, M J a Jonas, M a Wiest, O a

a UNIVERSITY OF NOTRE DAME (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVE ENZYMATIC RESOLUTIONS;

AMINO ACIDS; CONFORMATIONS; ESTERS; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHEMICAL REACTIONS;

PROLINE DERIVATIVE;

ARTICLE; CALCULATION; CONFORMATIONAL TRANSITION; CYCLIZATION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

AMIDES; CYCLOPENTANES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITROSO COMPOUNDS; PEPTIDES; PROLINE; STEREOISOMERISM;

EID: 0035823159 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo010284l Document Type: Article

Times cited : (29)

References (105)

1
- 0030768259
- (1997) Tetrahedron , vol.53 , pp. 12789
- Hanessian, S.¹ McNaughton-Smith, G.² Lombart, H.-G.³ Lubell, W.D.⁴

2
- 0001515091
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4228
- Dado, G.P.¹ Gellman, S.H.²

3
- 0027975871
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 1054
- Dado, G.P.¹ Gellman, S.H.²

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

5
- 0033577324
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2309
- Appella, D.H.¹ Barchi, J.J.² Durell, S.R.³ Gellman, S.H.⁴

6
- 0000291574
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 4105
- Haque, T.S.¹ Little, J.C.² Gellman, S.H.³

7
- 0029931671
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975
- Haque, T.S.¹ Little, J.C.² Gellman, S.H.³

8
- 0001074410
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 925
- Liang, G.-B.¹ Desper, J.M.² Gellman, S.H.³

9
- 0029139422
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3280
- Gardner, R.R.¹ Liang, G.-B.² Gellman, S.H.³

10
- 0001515091
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4228
- Dado, G.P.¹ Gellman, S.H.²

11
- 0000802654
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 1164
- Gellman, S.H.¹ Dado, G.P.² Liang, G.-B.³ Adams, B.R.⁴

12
- 0032918845
- (1999) Helv. Chim. Acta , vol.82 , pp. 1
- Gademann, K.¹ Jaun, B.² Seebach, D.³

13
- 0032431413
- (1998) Helv. Chim. Acta , vol.81 , pp. 2218
- Seebach, D.¹ Abele, S.² Sifferlen, T.³ Hanggi, M.⁴ Gruner, S.⁵ Seiler, P.⁶

14
- 0032884787
- (1999) Helv. Chim. Acta , vol.82 , pp. 1559
- Abele, S.¹ Seller, P.² Seebach, D.³

15
- 0345466641
- (1999) Helv. Chim. Acta , vol.82 , pp. 1539
- Abele, S.¹ Vogtli, K.² Seebach, D.³

16
- 0030811193
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 5413
- Nowick, J.S.¹ Pairish, M.² Lee, I.Q.³ Holmes, D.L.⁴ Ziller, J.W.⁵

17
- 0029670181
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2764
- Nowick, J.S.¹ Holmes, D.L.² Mackin, G.³ Noronha, G.⁴ Shaka, A.J.⁵ Smith, E.M.⁶

18
- 0033515658
- (1999) J. Org. Chem. , vol.64 , pp. 2176
- Gung, B.W.¹ Zou, D.² Stalcup, A.M.³ Cottrell, C.E.⁴

19
- 0030879441
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 6461
- Austin, R.E.¹ Maplestone, R.A.² Sefler, A.M.³ Liu, K.⁴ Hruzewicz, W.N.⁵ Liu, C.W.⁶ Cho, H.S.⁷ Wemmer, D.E.⁸ Bartlett, P.A.⁹

20
- 0000168053
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 11173
- Winningham, M.J.¹ Sogah, D.Y.²

21
- 0032569174
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8569
- Hanessian, S.¹ Luo, X.² Schaum, R.³ Michnick, S.⁴

22
- 0011034289
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3988
- Tsang, K.Y.¹ Diaz, H.² Graciani, N.³ Kelly, J.W.⁴

23
- 84936887577
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 8316
- Diaz, H.¹ Espina, J.R.² Kelly, J.W.³

24
- 0030457120
- and references therein
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 12261
- Eberhardt, E.S.¹ Panasik, N.² Raines, R.T.³

25
- 0021219016
- (1984) Biochim. Biophys. Acta , vol.800 , pp. 59
- Turpeenniemi-Hujanen, T.¹ Myllyla, R.²

26
- 0016711868
- (1975) Biochemistry , vol.14 , pp. 4953
- Brandts, J.F.¹ Halverson, H.R.² Brennan, M.³

27
- 0003893260
- (1984) Angew Chem., Int. Ed. Engl. , vol.23 , pp. 395
- Jaenicke, R.¹

28
- 84990485092
- (1985) Biopolymers , vol.24 , pp. 251
- Wetfauler, D.B.¹

29
- 0003893262
- (1986) Proc. Natl. Acad. Sci. U.S.A. , vol.6 , pp. 259
- Schmid, F.X.¹ Grafl, R.² Wrba, A.³ Beintema, J.J.⁴

30
- 0027442575
- (1993) Nature , vol.365 , pp. 847
- Suchyna, T.M.¹ Xu, L.X.² Gao, F.³ Fourtner, C.R.⁴ Nicholson, B.J.⁵

31
- 0027398959
- (1993) Eur. J. Biochem. , vol.212 , pp. 305
- Vogel, H.¹ Nilsson, L.² Rigler, R.³ Meder, S.⁴ Boheim, G.⁵ Beck, W.⁶ Kurth, H.H.⁷ Jung, G.⁸

32
- 0026738916
- (1992) J. Biol. Chem. , vol.267 , pp. 9474
- Jayaraman, T.¹ Brillantes, A.-M.² Timerman, A.P.³ Fleisher, S.⁴ Erdjument-Bromage, H.⁵ Tempst, P.⁶ Marks, A.R.⁷

33
- 0025326647
- (1990) Biochem. Pharm. , vol.40 , pp. 119
- Richards, N.G.J.¹ Hinds, M.G.² Brennand, D.M.³ Glennie, M.J.⁴ Welsh, J.M.⁵ Robinson, J.A.⁶

34
- 0027439867
- (1993) Crit. Rev. Biochem. Mol. Biol. , vol.28 , pp. 31
- Yaron, A.¹ Naider, F.²

35
- 0028670805
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 11931
- Fischer, S.¹ Dunbrack, R.L.² Karplus, M.³

36
- 33847087323
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 4855
- Madison, V.¹ Kopple, K.D.²

37
- 0001490908
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6635
- Delaney, N.G.¹ Madison, V.²

38
- 0000535768
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 5437
- Eberhardt, E.S.¹ Loh, S.N.² Hinck, A.P.³ Raines, R.T.⁴

39
- 0032503605
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 5568
- Scherer, G.¹ Kramer, M.L.² Schutkowski, M.³ Reimer, U.⁴ Fischer, G.⁵

40
- 0031028387
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 918
- Dumy, P.¹ Keller, M.² Ryan, D.E.³ Rohwedder, B.⁴ Wohr, T.⁵ Mutter, M.⁶

41
- 0001439872
- (1996) J. Org. Chem. , vol.61 , pp. 1385
- McDonald, Q.D.¹ Still, W.C.²

42
- 0030603082
- (1996) Tetrahedron Lett. , vol.37 , pp. 6235
- Zhang, R.¹ Madalengoitia, J.S.²

43
- 84985715908
- (1981) Biopolymers , vol.20 , pp. 2623
- Grathwol, C.¹ Wuthrich, K.²

44
- 0025260865
- (1990) Biochemistry , vol.29 , pp. 2205
- Fischer, G.¹ Schmid, F.X.²

45
- 0026030568
- (1991) Science , vol.251 , pp. 283
- Schreiber, S.L.¹

46
- 0026584271
- (1992) Nature , vol.355 , pp. 33
- Gething, M.-J.¹ Sambrook, J.²

47
- 0003843015
- (1992) Curr. Biol. , vol.2 , pp. 18
- Cyert, M.S.¹

48
- 0033592497
- (1999) Org. Lett. , vol.1 , pp. 1225
- Curran, T.P.¹ Marcaurelle, L.A.² O'Sullivan, K.M.³

49
- 0028852455
- (1995) Tetrahedron Lett. , vol.36 , pp. 191
- Curran, T.P.¹ McEnaney, P.M.²

50
- 0026514079
- (1992) J. Org. Chem. , vol.57 , pp. 202-209
- Zabrocki, J.¹ Dunbar, J.B.² Marshall, K.W.³ Toth, M.V.⁴ Marshall, G.R.⁵

51
- 0029151753
- (1995) Helv. Chim. Acta , vol.78 , pp. 1588
- Gramberg, D.¹ Weber, C.² Beeli, R.³ Inglis, J.⁴ Bruns, C.⁵ Robinson, J.A.⁶

52
- 0000325130
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5927
- Chalmers, D.K.¹ Marshall, G.R.²

53
- 0027941641
- (1994) Tetrahedron Lett. , vol.35 , pp. 9379
- Ritter, A.R.¹ Miller, M.J.²

54
- 0029928959
- (1996) J. Org. Chem. , vol.61 , pp. 4838
- Heinz, L.J.¹ Lunn, W.H.W.² Murff, R.E.³ Paschal, J.W.⁴ Spangle, L.A.⁵

55
- 0010745317
- (1977) Chem. Soc. Rev. , vol.6 , pp. 1
- Kirby, G.W.¹

56
- 84987553700
- (1992) Helv. Chim. Acta , vol.75 , pp. 109
- Defoin, A.¹ Brouillard-Poichet, A.² Streith, J.³

57
- 0003900777
- (1996) Synlett , vol.189
- Streith, J.¹ Defoin, A.²

58
- 0003789309
- (1994) Synthesis , vol.1107
- Streith, J.¹ Defoin, A.²

59
- 0032546129
- (1998) Tetrahedron , vol.54 , pp. 1317
- Vogt, P.F.¹ Miller, M.J.²

60
- 0000556633
- (1994) J. Org. Chem. , vol.59 , pp. 4602
- Ritter, A.R.¹ Miller, M.J.²

61
- 0034597973
- (2000) Tetrahedron Lett. , vol.41 , pp. 9537
- Shireman, B.T.¹ Miller, M.J.²

62
- 0003920346
- (1995) J. Org. Chem. , vol.60 , pp. 8
- Ghosh, A.¹ Ritter, A.R.² Miller, M.J.³

63
- 0030914234
- (1997) Tetrahedron Lett. , vol.38 , pp. 2803
- Vogt, P.F.¹ Hansel, J.G.² Miller, M.J.³

64
- 0031306301
- (1997) Enantiomer , vol.2 , pp. 367-380
- Vogt, P.F.¹ Miller, M.J.² Mulvihill, M.J.³ Ramurthy, S.⁴ Savela, G.C.⁵ Ritter, A.R.⁶

65
- 0028941858
- (1995) Tetrahedron Lett. , vol.36 , pp. 2913
- Hansel, J.-G.¹ O'Hogan, S.² Lensky, S.³ Ritter, A.R.⁴ Miller, M.J.⁵

66
- 0024845709
- (1989) Tetrahedron Lett. , vol.30 , pp. 7061
- Brouillard-Poichet, A.¹ Defoin, A.² Streith, J.³

67
- 0033522737
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2165
- Faitg, T.¹ Soulie, J.² Lallemand, J.-Y.³ Ricard, L.⁴

68
- 0001291097
- (1979) J. Org. Chem. , vol.44 , pp. 2487
- Lee, V.J.¹ Woodward, R.B.²

69
- 0033608080
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 587
- Wu, M.¹ Moon, H.-S.² Begley, T.P.³ Myllyharju, J.⁴ Kivirikko, K.I.⁵

70
- 0000714394
- (1993) Tetrahedron Lett. , vol.34 , pp. 819
- Wess, G.¹ Kramer, W.² Schubert, G.³ Enhsen, A.K.-H.⁴ Baringhaus, K.-H.⁵ Glombik, H.⁶ Mullner, S.⁷ Bock, K.⁸ Kleine, H.⁹ John, M.¹⁰ Neckerman, G.¹¹ Hoffman, A.¹²

71
- 0003772264
- (1981) Chem. Commun. , vol.97
- Vasella, A.¹ Voeffray, R.²

72
- 0020609509
- (1983) Helv. Chim. Acta , vol.66 , pp. 1241
- Vasella, A.¹ Voeffray, R.² Pless, J.³ Huguenin, R.⁴

73
- 0035854289
- (2001) J. Org. Chem. , vol.66 , pp. 4809
- Shireman, B.T.¹ Miller, M.J.²

74
- 0003175380
- (1982) Tetrahedron , vol.39 , pp. 1753
- Kolasa, T.¹

75
- 0003900779
- (1967) Chem. Commun. , vol.1070
- Price, B.J.¹ Sutherland, I.O.²

76
- 0020094427
- (1982) Int. J. Pept. Protein Res. , vol.19 , pp. 123
- Galardy, R.E.¹ Alger, J.R.² Liakopoulou-Kyriakides, M.³

77
- 0029860639
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9794
- Yang, D.¹ Ng, F.F.² Li, Z.J.³ Wu, Y.D.⁴ Chan, K.W.K.⁵ Wang, D.-P.⁶

78
- 0003916524
- (1999) J. Am. Chem. Soc. , vol.589
- Yang, D.¹ Qu, J.² Li, B.³ Ng, F.F.⁴ Wang, X.C.⁵ Cheung, K.K.⁶ Wang, D.-P.⁷ Wu, Y.D.⁸

79
- 0033537027
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11189
- Wu, Y.D.¹ Wang, D.-P.² Chan, K.W.K.³ Yang, D.⁴

80
- 0034602350
- (2000) J. Org. Chem. , vol.65 , pp. 7667
- Shin, I.¹ Lee, M.-R.² Lee, J.³ Jung, M.⁴ Lee, W.⁵ Yoon, J.⁶

81
- 0002793634
- (1989) Synlett , vol.1 , pp. 32-34
- Miller, A.¹ Paterson, T.M.² Procter, G.³

82
- 0026634836
- (1992) Tetrahedron Lett. , vol.33 , pp. 3583-3585
- Martin, S.F.¹ Hartmann, M.² Josey, J.A.³

83
- 2542433188
- (1981) J. Org. Chem. , vol.46 , pp. 3936
- Carlsen, H.J.¹ Katsuki, T.² Martin, V.S.³ Sharpless, B.K.⁴

84
- 12044258245
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397
- Carpino, L.A.¹

85
- 0003789311
- (1995) J. Chem. Soc., Perkin Trans. 1 , vol.1639
- Dunn, M.J.¹ Gomez, S.² Jacksom, R.F.W.³

86
- 0023259926
- (1987) J. Med. Chem. , vol.30 , pp. 1074
- Graham, D.W.¹ Ashton, W.T.² Barash, L.³ Brown, J.E.⁴ Brown, R.D.⁵ Canning, L.F.⁶ Chen, A.⁷ Springer, J.P.⁸ Rogers, E.F.⁹

87
- 0018344725
- (1979) Tetrahedron Lett. , vol.6 , pp. 521
- Nomoto, S.¹ Sano, A.² Shiba, T.³

88
- 0003900781
- (1980) J. Org. Chem. , vol.45 , pp. 5
- Miller, M.J.¹

89
- 0000637984
- (1986) J. Org. Chem. , vol.51 , pp. 106
- Lee, B.H.¹ Biswas, A.² Miller, M.J.³

90
- 0003900783
- (1994) Synthesis , vol.1096
- Endo, Y.¹ Uchida, T.² Hizatate, S.³ Shudo, K.⁴

91
- 0034682149
- (2000) Org. Lett. , vol.2 , pp. 1345
- Wu, M.¹ Begley, T.P.²

92
- 0027456373
- (1993) Tetrahedron Lett. , vol.34 , pp. 961
- Desai, M.C.¹ Doty, J.L.² Stephens, L.M.³ Brighty, K.E.⁴

93
- 0032489023
- (1998) J. Org. Chem. , vol.63 , pp. 755
- Zhang, D.¹ Miller, M.J.²

94
- 0003831278
- note

95
- 0025014627
- (1990) Tetrahedron Lett. , vol.31 , pp. 205
- Coste, J.¹ Le-Nguyen, D.² Castro, D.³

96
- 0003857657
- note

97
- 0003782005
- (1979) Synthesis , vol.561
- Mathias, L.J.¹

99
- 84961985847
- (1998) Phys. Chem. A , vol.102 , pp. 1995
- Barone, V.¹ Cossi, M.J.²

100
- 84962420539
- (2000) J. Org. Chem. , vol.65 , pp. 7930
- Rablen, P.R.¹

101
- 0034607389
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3151
- Nielsen, P.A.¹ Norrby, P.O.² Liljefors, T.³ Rega, N.⁴ Barone, V.⁵

102
- 0001160236
- (1978) Tetrahedron Lett. , vol.35 , pp. 3275
- Kost, D.¹ Kornberg, N.²

103
- 0000117881
- (1996) J. Org. Chem. , vol.61 , pp. 8402
- Marcovici-Mizrahi, D.¹ Gottlieb, H.E.² Marks, V.³ Nudelman, A.⁴

104
- 0000459942
- (1998) J. Org. Chem. , vol.63 , pp. 7258
- Moraczewski, A.L.¹ Banaszynski, L.A.² From, A.M.³ White, C.E.⁴ Smith, B.D.⁵

105
- 0001625628
- (2000) Org. Lett. , vol.2 , pp. 1247
- Blank, J.T.¹ Guerin, D.J.² Miller, S.J.³

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