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Volumn 1989, Issue 12, 1989, Pages 1215-1232

Synthesis of Nonproteinogenic (R)‐ or (S)‐Amino Acids Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert‐Butyl 2‐(tert‐Butyl)‐3‐methyl‐4‐oxo‐1‐imidazolidinecarboxylate (Boc‐BMI)

(5) Seebach, Dieter a Dziadulewicz, Edward a Behrendt, Linda a Cantoreggi, Sergio a Fitzi, Robert a

a ETH ZURICH (Switzerland)

Author keywords

Diamino dicarboxylic acids; Glycine enolate derivatives, chiral; Lithium enolates, reactivity of; Amino acids, 4 to 7 membered heterocyclic; Deuterio amino acids

Indexed keywords

EID: 84986674631 PISSN: 01702041 EISSN: 10990690 Source Type: Journal
DOI: 10.1002/jlac.198919890293 Document Type: Article

Times cited : (138)

References (98)

1
- 84986660643
- Fellow of the exchange programme between the Royal Society and the Schweizerische Nationalfonds zur Förderung der wissenschaftlichen Forschung 1987/1988.

2
- 84986660641
- Part of the Diplomarbeit. of L. B. and S. C., ETH Zürich, 1989, respectively

3
- 0001654036
- (1983) Angew. Chem. , vol.95 , pp. 827
- Wagner, I.¹ Musso, H.²

4
- 0348183819
- (1983) Angew. Chem. Int. Ed. Engl. , vol.22 , pp. 816

5
- 33845278130
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1547
- Williams, R.M.¹ Sinclair, P.J.² Zhai, D.³ Chen, D.⁴

6
- 0001149779
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 278
- Ojima, I.¹ Chen, H.‐J.C.² Nakahashi, K.³

7
- 0000242199
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 4649
- Arnold, L.D.¹ Drover, J.C.G.² Vederas, J.C.³

8
- 0003828324
- G. C. Barrett, Chapman and Hall, London
- (1985) Chemistry and Biochemistry of the Amino Acids

9
- 0000035859
- Tetrahedron Symposia‐in‐Print, Number 31
- (1988) Tetrahedron , vol.44 , pp. 661-1006
- Hruby, V.J.¹ Schwyzer, R.²

10
- 0000727735
- (1982) Angew. Chem. , vol.94 , pp. 590
- Drauz, K.¹ Kleemann, A.² Martens, J.³

11
- 0020173565
- (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 584

12
- 0003899348
- Wiley‐Interscience, New York
- (1987) Asymmetric Synthesis: Comstruction of Chiral Molecules Using Amino Acids
- Coppola, G.M.¹ Schuster, H.F.²

13
- 0003598098
- R. Scheffold, Springer‐Verlag, Berlin – Heidenberg – New York – Tokyo
- (1986) Modern Synthetic Methods 1986 , vol.4 , pp. 125-260
- Seebach, D.¹ Imwinkelried, R.² Weber, T.³

14
- 84918753335
- Modern Asymmetric Synthesis of α-Aminoacids
- 12a
- (1987) Russian Chemical Reviews , vol.56 , pp. 1045
- Kochetkov, K.A.¹ Belikov, V.M.²

15
- 0002846446
- Enantioselective synthesis of nonproteinogenic amino acids
- 12b
- (1983) Topics Curr. Chem. , vol.109 , pp. 65
- Schöllkopf, U.¹

16
- 84913964779
- 12c
- (1988) Nachr. Chem. Tech. Lab. , vol.36 , pp. 999
- Altenbach, H.‐J.¹

17
- 0001039009
- Tetrahedron Symposia‐in‐Print, Number 33
- (1988) Tetrahedron , vol.44 , pp. 5253-5614
- O'Donnel, M.J.¹

18
- 1542692819
- Enantiomerentrennung von (R,S)-2-(tert-Butyl)-3-methyl-4-imidazolidinon, einem chiralen Baustein für die Aminosäuresynthese
- 14a
- (1986) Angewandte Chemie , vol.98 , pp. 363
- Fitzi, R.¹ Seebach, D.²

19
- 84918174529
- Erratum
- (1986) Angew. Chem. , vol.98 , pp. 842

20
- 84985579913
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 345

21
- 84985598502
- Erratum
- (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 766

22
- 0001291259
- 14b
- (1988) Tetrahedron , vol.44 , pp. 5277
- Fitzi, R.¹ Seebach, D.²

23
- 84986706514
- 15a, Ph. D. Thesis., No. 8616, ETH Zürich
- (1988)
- Müller, S.G.¹

24
- 0001269688
- 15b
- (1988) Helvetica Chimica Acta , vol.71 , pp. 1303
- Seebach, D.¹ Müller, S.G.² Gysel, U.³ Zimmermann, J.⁴

25
- 84986706532
- 14,0.17.

26
- 0016704846
- 17a
- (1975) Eur. J. Biochem. , vol.55 , pp. 431
- Hennecke, H.¹ Böck, A.²

27
- 84986639196
- 17b, in Abstract Book of the 14th International Congress of Biochemistry. (No. TH0.009), Prague, July
- (1988) , pp. 10-15
- Kast, P.¹ Hennecke, H.²

28
- 0015215617
- (1971) J. Org. Chem. , vol.36 , pp. 3019
- Thanassi, J.W.¹

29
- 0021474044
- (1984) Bull. Chem. Soc. Jpn. , vol.57 , pp. 2193
- Tanimura, K.¹ Kato, T.² Waki, M.³ Lee, S.⁴ Kodera, Y.⁵ Izumiya, N.⁶

30
- 0003697122
- 0.19.
- (1971) Deuterium Labelling in Organic Chemistry
- Thomas, A.F.¹

31
- 0023219599
- (1987) J. Org. Chem. , vol.52 , pp. 3326
- Reider, P.J.¹ Conn, R.S.E.² Davis, P.³ Grenda, V.J.⁴ Zambita, A.J.⁵ Grabowski, E.J.J.⁶

32
- 37049112292
- 23a, J. Chem. Soc., Chem. Commun.
- (1985) , pp. 1496
- Baldwin, J.E.¹ Adlington, R.M.² Lajoie, G.A.³ Rawlings, B.J.⁴

33
- 0001051036
- 23b
- (1988) Tetrahedron Lett. , vol.29 , pp. 3315
- Aitker, D.J.¹ Royer, J.² Husson, H.‐P.³

34
- 0141688445
- 24a
- (1987) J. Org. Chem. , vol.52 , pp. 15
- Subramanian, P.K.¹ Woodard, R.W.²

35
- 0024510909
- 24b
- (1989) J. Org. Chem. , vol.54 , pp. 270
- Subramanian, P.K.¹ Kalvin, D.M.² Ramalingam, K.³ Woodard, R.W.⁴

36
- 0000653159
- Synthesis of stereospecific deuterium-labeled homoserines and homoserine lactones
- 24c, 1900.
- (1988) The Journal of Organic Chemistry , vol.53
- Ramalingam, K.¹ Woodard, R.W.²

37
- 84986639244
- Ph. D. Thesis., No. 8003, ETH Zürich
- (1987)
- Wiesendanger, R.¹

38
- 0000561351
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 795
- Hill, R.K.¹ Prakash, S.R.² Wiesendanger, R.³ Angst, W.⁴ Martinoni, B.⁵ Arigoni, D.⁶ Liu, W.H.⁷ Walsh, C.T.⁸

39
- 37049073403
- J. Chem. Soc., Chem. Commun.
- (1986) , pp. 238
- Wiesendanger, R.¹ Martinoni, B.² Boller, T.³ Arigoni, D.⁴

40
- 84986727574
- 0.32.

41
- 84986360482
- Preparation and C-Alkylation of Enantiomerically PureS-Phenyl Aziridinecarbothioates. On the Structure of Small-Ring Ester Lithium Enolates
- (1987) Helvetica Chimica Acta , vol.70 , pp. 1676
- Häner, R.¹ Olano, B.² Seebach, D.³

42
- 0023883642
- (1988) J. Org. Chem. , vol.53 , pp. 2103
- Molinski, T.F.¹ Ireland, C.M.²

43
- 0001574305
- 29a
- (1981) Heterocycles , vol.15 , pp. 819
- Fushiya, S.¹ Nakatsuyama, S.² Sato, Y.³ Nozoe, S.⁴

44
- 0014682610
- 29b
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 7490
- Isono, K.¹ Asahi, K.² Suzuki, S.³

45
- 84986643845
- 29c, Diplomarbeit., ETH Zürich
- (1988)
- Müller, H.‐M.¹

46
- 33845551868
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 5390
- Seebach, D.¹ Boes, M.² Naef, R.³ Schweizer, W.B.⁴

47
- 3643118353
- Asymmetrische Synthese cyclischer α-Aminosäuren nach der Bislactimether-Methode
- (1987) Angewandte Chemie , vol.99 , pp. 137
- Schöllkopf, U.¹ Hinrichs, R.² Lonsky, R.³

48
- 84985520734
- (1987) Angew. Chem. Int. Ed. Engl. , vol.26 , pp. 143

49
- 0022751007
- 32a
- (1987) J. Mol. Catalysis , vol.41 , pp. 135
- Izawa, K.¹ Nishi, S.² Asada, S.³

50
- 85004654482
- Synthesis of N-acyl-.ALPHA.-amino acids by cobalt catalyzed amido-carbonylation.
- (1988) Journal of Synthetic Organic Chemistry, Japan , vol.46 , pp. 218
- Izawa, K.¹

51
- 0001473435
- 32b
- (1986) Heterocycles , vol.24 , pp. 2165
- Bajgrowicz, J.¹ El Achquar, A.² Roumestant, M.‐L.³ Pigière, C.⁴ Viallefont, P.⁵

52
- 84986686146
- We are proceeding towards more highly functionalized derivatives of type C and D; the results will be described separately.

53
- 84986690453
- Only with benzyl chlorides, such as in the preparation of 1e, is warming to higher temp. necessary for completion of the reaction.

54
- 84987564680
- (1985) Helvetica Chimica Acta , vol.68 , pp. 1373
- Laube, T.¹ Dunitz, J.D.² Seebach, D.³

55
- 0001269629
- Struktur und Reaktivität von Lithiumenolaten, vom Pinakolon zur selektivenC-Alkylierung von Peptiden – Schwierigkeiten und Möglichkeiten durch komplexe Strukturen
- (1988) Angewandte Chemie , vol.100 , pp. 1685
- Seebach, D.¹

56
- 84990085779
- (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 1624

57
- 0001089836
- 13C‐NMR spectroscopy, complete conversion occurring within 2 min after completion of addition of BuLi
- (1988) J. Org. Chem. , vol.53 , pp. 2643
- Podraza, K.F.¹ Bassfield, R.L.²

58
- 84985052504
- Substitution of HMPT by the cyclic urea DMPU as a cosolvent for highly reactive nucleophiles and bases
- (1982) Helvetica Chimica Acta , vol.65 , pp. 385
- Mukhopadhyay, T.¹ Seebach, D.²

59
- 84986660667
- 32b, Viallefont et al. have described the synthesis of cyclic and open‐chain halogeno amino acid derivatives, using similar strategy: alkylation with an α,ω‐dihalogeno electrophile gives a monohalogeno intermediate which is cyclized to the desired product.

60
- 84986690470
- 1H‐NMR spectra believed to be due to the existence of rotamers.

61
- 84986686158
- 0.14). Attempted 8‐membered ring formation from 12 (R = Me; n = 0.6) yields the iodo analogue of 13 in 61% yield [calcd. from ( S)‐Boc‐BMI].

62
- 0023197715
- 33b, . ( S)‐2‐Amino‐4‐chloro‐4‐pentenoic acid is known to exhibit antibacterial activity
- (1987) J. Antibiot. , vol.40 , pp. 904
- Moriguchi, M.¹ Hara, Y.² Hatanaka, S.‐I.³

63
- 84986706608
- 3; n = 0.3) cyclizes spontaneously upon hydrogen carbonate treatment after the (acidic) Boc removal.

64
- 0015969719
- 44a
- (1974) J. Org. Chem. , vol.39 , pp. 104
- Ellington, J.J.¹ Honigberg, I.L.²

65
- 0017504903
- 44b
- (1977) J. Polym. Sci., Polym. Chem. Ed. , vol.15 , pp. 1413
- Overberger, C.G.¹ Jon, Y.S.²

66
- 0020625909
- (1983) Chem. Pharm. Bull. , vol.31 , pp. 312
- Hayashi, K.¹ Ozaki, Y.² Nunami, K.I.³ Yoneda, N.⁴

67
- 84986660678
- Ph. D Thesis., No. 8397, ETH Zurich
- (1987)
- Huber, I.¹

68
- 84986649343
- The iodo compound 22 was used precisely because we did not know at the outset whether the basicity or nucleophilicity of the enolate of 21 would dominate with the corresponding chloro precursor. In using compounds 12 as alkylating agents (when R ≠ H), halide exchange need not be carried out, but the reactions should be conducted in the presence of DMPU.

69
- 84987505887
- (1987) Helv. Chim. Acta , vol.70 , pp. 237
- Seebach, D.¹ Juaristi, E.² Miller, D.D.³ Schickli, C.⁴ Weber, T.⁵

70
- 84956106373
- N,O-Acetals from Pivalaldehyde and Amino Acids for the ?-Alkylation with Self-Reproduction of the Center of Chirality. Enolates of 3-Benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones
- (1985) Helvetica Chimica Acta , vol.68 , pp. 1243
- Seebach, D.¹ Fadel, A.²

71
- 84986719084
- In the construction of type B amino acids from oxazolidinones, the use of BuLi is not tolerated in the case of the phenylalanine‐derived cycle although it is to a greater extent with that from methionine. However, even simple deprotonation and reprotonation of oxazolidinone derivatives is not selective, and 1:1 mixtures of diastereoisomers are formed; the presence of additional reaction components voids the relative simplicity of this synthetic operation.

72
- 0002714675
- (1978) J. Org. Chem. , vol.43 , pp. 2923
- Still, W.C.¹ Kahn, M.² Mitra, A.³

73
- 84982336567
- Verbesserung und Erweiterung der Bromierungsmethode mit Brom-succinimid
- (1946) Helvetica Chimica Acta , vol.29 , pp. 573
- Schmid, H.¹ Karrer, P.²

74
- 0004055425
- 2nd Edition, Pergamon Press, Oxford
- (1980) Purification of Laboratory Chemicals
- Perrin, D.D.¹ Armarego, W.L.F.² Perrin, D.R.³

75
- 0021988374
- TLC on Chiralplate (Macherey‐Nagel, Düren, West Germany).
- (1985) Naturwissenschaften , vol.72 , pp. 149
- Günther, K.¹ Schickedanz, M.²

76
- 84982482243
- Brom-Lithium-Austausch an Vinyl- und Aryl-bromiden mittert-Butyllithium Zur Ringerweiterung über Dibromcarbenaddukte
- (1974) Chemische Berichte , vol.107 , pp. 847
- Seebach, D.¹ Neumann, H.²

77
- 0000464825
- (1963) Org. Synth., Coll , vol.4 , pp. 921
- Campaigne, E.¹ Tullar, B.F.²

78
- 0010627551
- Elimination and Replacement Reactions of dl-erythro- and dl-threo-2-Deutero-1,2-diphenylethanol and Derivatives1,2
- 57a
- (1953) Journal of the American Chemical Society , vol.75 , pp. 6011
- Curtin, D.Y.¹ Kellom, D.B.²

79
- 84986711909
- 57b, – The base‐induced coupling has been observed previously
- (1974) Synth. Commun. , vol.9 , pp. 11
- Wenkert, E.¹ Bakuzis, P.² Dynak, J.N.³ Swindell, C.S.⁴

80
- 84986649373
- J. Chem. Soc.
- (1952) , pp. 5044
- Chapman, N.B.¹ Williams, J.F.A.²

81
- 0016333027
- (1974) Anal. Biochem. , vol.62 , pp. 615
- Faulstich, H.¹ Trischmann, H.²

82
- 0015101773
- (1971) Can. J. Biochem. , vol.49 , pp. 877
- Tong, J.H.¹ Petitclerc, C.² D'Iorio, A.³ Leo Benoiton, N.⁴

83
- 33947455200
- (1950) J. Am. Chem. Soc. , vol.72 , pp. 1800
- Bennett, E.L.¹ Niemann, C.²

84
- 0019826015
- (1981) Peptides , vol.2 , pp. 251
- Erchegy, J.¹ Coy, D.H.² Nekola, M.V.³ Pedroza, E.⁴ Coy, E.J.⁵ Mezo, I.⁶ Shally, A.V.⁷

85
- 84986688616
- We suspect that some decomposition occurs during hydrolysis.

86
- 0017576129
- A lower hydrolysis temp. was chosen in this instance as a precautionary measure, as Ar‐H/Ar‐D exchange has been previously observed by others:, (although see 2b)
- (1977) Biochim. Biophys. Acta , vol.497 , pp. 1
- Matthews, H.R.¹ Matthews, K.S.² Opella, S.J.³

87
- 84986713336
- Deuterated amino acids. IV. The synthesis ofL-phenyld5-alanine-2,3,3-d3
- (1968) Canadian Journal of Chemistry , vol.46 , pp. 1053
- Blomquist, A.T.¹ Cadergren, R.J.²

88
- 0017033663
- (1976) Chem. Pharm. Bull. , vol.24 , pp. 3149
- Yabe, Y.¹ Miura, C.² Horikoshi, H.³ Baba, Y.⁴

89
- 84986718919
- The reaction had been initially carried out on a smaller scale using ( R)‐(+)‐Boc‐BMI to yield 86% of ent‐3a

90
- 84986685240
- The reaction had been initially carried out on a smaller scale using (R)‐(+)‐Boc‐BMI to yield 79% ofent‐3b.

91
- 2442606882
- (1948) J. Am. Chem. Soc. , vol.70 , pp. 1756
- Armstrong, M.D.¹

92
- 84986685249
- Smaller amounts of THF are sufficient and more convenient in reactions on a scale greater than 5 mmol; the total volume used for 12b for example was 80 ml of THF without any difficulties.

93
- 84986719137
- Compound 14d has also been synthesized directly from (S)‐Boc‐BMI in 61% yield without needing to purify either 12d or 13d; this represents an avergage of 85% yield for each of the three steps.

94
- 84986685255
- 5 for ca. 18 h [m. p. 202–205° (dec.)].

95
- 0343949803
- (1983) Eur. Polymer J. , vol.19 , pp. 1055
- Overberger, C.G.¹ Shalati, M.D.²

96
- 84986643215
- (Teijin Ltd.)
- (1978) Jpn. Kokai , vol.78 , pp. 28153
- Wakabayashi, T.¹ Kato, Y.² Watanabe, K.³

97
- 84986643216
- (1978) Chem. Abstr. , vol.89 , pp. 42904

98
- 0018696782
- 1931
- (1979) Chem. Pharm. Bull. , vol.27
- Yasuo, H.¹ Suzuki, M.² Yoneda, N.³

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