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20
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0001188647
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This trifunctional amino acid(propargylglycine) is commercially available, but in our group also readily prepared via a chemo-enzymatic procedure that has been developed in collaboration with DSM Research (Geleen, The Netherlands): (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000, 23.
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21
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0002267204
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Patel, R. N., Ed.; Marcel Dekker: New York
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This trifunctional amino acid(propargylglycine) is commercially available, but in our group also readily prepared via a chemo-enzymatic procedure that has been developed in collaboration with DSM Research (Geleen, The Netherlands): (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000, 23.
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Sonke, T.1
Kaptein, B.2
Boesten, W.H.J.3
Broxterman, Q.B.4
Kamphuis, J.5
Formaggio, F.6
Toniolo, C.7
Rutjes, F.P.J.T.8
Schoemaker, H.E.9
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23
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0037733052
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IJsselstijn, M.1
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Rutjes, F.P.J.T.5
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24
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0034700645
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Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker, H. E. J. Chem. Soc., Perkin Trans. 1 2000, 4197.
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Rutjes, F.P.J.T.1
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Schoemaker, H.E.3
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25
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0347812008
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note
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13C NMR, high resolution mass data and rotational values.
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26
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0037124432
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Similar elimination of p-toluenesulfinic acid from sulfonamide moieties has previously been observed: (a) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491. (b) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S.; Sacramento, J. J. Chem. Soc., Perkin Trans. 1 2001, 3167.
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 4491
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Ferreira, P.M.T.1
Maia, H.L.S.2
Monteiro, L.S.3
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27
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0035544082
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Similar elimination of p-toluenesulfinic acid from sulfonamide moieties has previously been observed: (a) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2002, 43, 4491. (b) Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S.; Sacramento, J. J. Chem. Soc., Perkin Trans. 1 2001, 3167.
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(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 3167
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Ferreira, P.M.T.1
Maia, H.L.S.2
Monteiro, L.S.3
Sacramento, J.4
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29
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0347812007
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note
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Crystallographic data of structures 21 and 26 have both been deposited at the Cambridge Crystallographic Data Centre and have been allocated the deposition numbers CCDC 212273 and CCDC 212274, respectively.
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30
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0345920782
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note
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To determine the enantiopurity of compound 24, racemic 24 was synthesised and separated on a Chiralcel OD column (eluant: i-PrOH/hexane = 1:9). Using this assay, the ee of pyrroline 24 was determined to be >99%.
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31
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0003473687
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Utrecht University, Utrecht, The Netherlands
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Spek, A. L. PLATON, A Multipurpose Crystallographic Tool, 2002, Utrecht University, Utrecht, The Netherlands.
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(2002)
PLATON, a Multipurpose Crystallographic Tool
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Spek, A.L.1
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33
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0347812006
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note
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4S: 359.1191. Found: 359.1183.
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