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supplementary material and refs. therein
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F.A. Davis, R.E. Reddy, J.M. Szewczyk, G.V. Reddy, P.S. Portonova, H. Zhang, D. Fanelli, R.T. Reddy, P. Zhou and P.J. Carrol, J. Org. Chem., 1997, 62, 2555, supplementary material and refs. therein.
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(c) D.R.J. Hose, M.F. Hahon, K.C. Molloy, T. Raynham and M. Wills, J. Chem. Soc., Perkin Trans. 1, 1996, 691.
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(d) T.-K. Yang, R.-Y. Chen, D.-S. Lee, W.-S. Peng, Y.-Z. Jiang, A.-Q. Mi and T.-T. Jong, J. Org. Chem., 1994, 59, 914.
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8
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0032358630
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F.A. Davis, P. Zhou and B.-C. Chen, Chem. Soc. Rev., 1998, 27, 13 and refs. therein.
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Davis, F.A.1
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9
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and refs. therein
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(a) A. Viso, R.F. de la Pradilla, C. Guerrero-Strachan, M. Alonosa, M. Martinez-Ripoll and I. Andre, J. Org. Chem., 1997, 62, 2316 and refs. therein.
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(b) K. Burger, J. Albanbauer, F. Kafig and S.S. Penninger, Liebigs Ann. Chem., 1977, 624.
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(c) T. Yoshida, S. Naruto, H. Uno and H. Nishimura, Chem. Pharm. Bull., 1982, 30, 2820.
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Yoshida, T.1
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0030561371
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J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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Reddy, G.V.2
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J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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0028139165
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J.L.G. Ruano, I. Fernandez, M.d P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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Davis, F.A.1
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18
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0029144508
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J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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Tetrahedron: Asymmetry
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Davis, F.A.1
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Liang, C.H.3
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-
19
-
-
0029883037
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-
J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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(1996)
Tetrahedron Lett.
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Davis, F.A.1
Reddy, G.V.2
-
20
-
-
0030605852
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-
J.L.G. Ruano, I. Fernandez, M.d.P. Catalina and A.A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407; J.L.G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295; F.A. Davis, G.V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651; F.A. Davis, P. Zhou and G.V. Reddy, J. Org. Chem., 1994, 59, 3243; F.A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525; F.A. Davis, P. Zhou, C.H. Liang and R.E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; F.A. Davis and G.V. Reddy, Tetrahedron Lett., 1996, 37, 4349; F.A. Davis, H. Liu and G.V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
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(1996)
Tetrahedron Lett.
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Davis, F.A.1
Liu, H.2
Reddy, G.V.3
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21
-
-
0000910788
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For leading references on the chemistry of sulfenic acids see: F.A. Davis, L.A. Jenkins and R.L. Billimers, J. Org. Chem., 1986, 51, 1033.
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(1986)
J. Org. Chem.
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Davis, F.A.1
Jenkins, L.A.2
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22
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0028875576
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F.A. Davis, R.E. Reddy and J.M. Szewczyk, J. Org. Chem., 1995, 60, 7037.
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(1995)
J. Org. Chem.
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Davis, F.A.1
Reddy, R.E.2
Szewczyk, J.M.3
-
23
-
-
0000409113
-
-
For leading references on the synthesis of amino acids using sulfinimines see refs. 3(b), 4, 8 also ref. 11 below and F.A. Davis, P.S. Portonova, R.E. Reddy and Y.-H. Chiu, J. Org. Chem., 1996, 61, 440; J. Jiang, K. Schumacher, M.M. Joullie, F.A. Davis and R.E. Reddy, Tetrahedron Lett., 1994, 35, 2121; F.A. Davis, J. Szewczyk and R.E. Reddy, J. Org. Chem., 1996, 61, 2222; T. Fujisawa, Y. Kooriyama and M. Shimizu, Tetrahedron Lett., 1996, 37, 3881; F.A. Davis and R.E. Reddy, Tetrahedron: Asymmetry, 1994, 5, 955.
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(1996)
J. Org. Chem.
, vol.61
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Davis, F.A.1
Portonova, P.S.2
Reddy, R.E.3
Chiu, Y.-H.4
-
24
-
-
0028198515
-
-
For leading references on the synthesis of amino acids using sulfinimines see refs. 3(b), 4, 8 also ref. 11 below and F.A. Davis, P.S. Portonova, R.E. Reddy and Y.-H. Chiu, J. Org. Chem., 1996, 61, 440; J. Jiang, K. Schumacher, M.M. Joullie, F.A. Davis and R.E. Reddy, Tetrahedron Lett., 1994, 35, 2121; F.A. Davis, J. Szewczyk and R.E. Reddy, J. Org. Chem., 1996, 61, 2222; T. Fujisawa, Y. Kooriyama and M. Shimizu, Tetrahedron Lett., 1996, 37, 3881; F.A. Davis and R.E. Reddy, Tetrahedron: Asymmetry, 1994, 5, 955.
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(1994)
Tetrahedron Lett.
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Jiang, J.1
Schumacher, K.2
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Davis, F.A.4
Reddy, R.E.5
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25
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-
0029876181
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For leading references on the synthesis of amino acids using sulfinimines see refs. 3(b), 4, 8 also ref. 11 below and F.A. Davis, P.S. Portonova, R.E. Reddy and Y.-H. Chiu, J. Org. Chem., 1996, 61, 440; J. Jiang, K. Schumacher, M.M. Joullie, F.A. Davis and R.E. Reddy, Tetrahedron Lett., 1994, 35, 2121; F.A. Davis, J. Szewczyk and R.E. Reddy, J. Org. Chem., 1996, 61, 2222; T. Fujisawa, Y. Kooriyama and M. Shimizu, Tetrahedron Lett., 1996, 37, 3881; F.A. Davis and R.E. Reddy, Tetrahedron: Asymmetry, 1994, 5, 955.
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Davis, F.A.1
Szewczyk, J.2
Reddy, R.E.3
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26
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0029940966
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For leading references on the synthesis of amino acids using sulfinimines see refs. 3(b), 4, 8 also ref. 11 below and F.A. Davis, P.S. Portonova, R.E. Reddy and Y.-H. Chiu, J. Org. Chem., 1996, 61, 440; J. Jiang, K. Schumacher, M.M. Joullie, F.A. Davis and R.E. Reddy, Tetrahedron Lett., 1994, 35, 2121; F.A. Davis, J. Szewczyk and R.E. Reddy, J. Org. Chem., 1996, 61, 2222; T. Fujisawa, Y. Kooriyama and M. Shimizu, Tetrahedron Lett., 1996, 37, 3881; F.A. Davis and R.E. Reddy, Tetrahedron: Asymmetry, 1994, 5, 955.
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Fujisawa, T.1
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27
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For leading references on the synthesis of amino acids using sulfinimines see refs. 3(b), 4, 8 also ref. 11 below and F.A. Davis, P.S. Portonova, R.E. Reddy and Y.-H. Chiu, J. Org. Chem., 1996, 61, 440; J. Jiang, K. Schumacher, M.M. Joullie, F.A. Davis and R.E. Reddy, Tetrahedron Lett., 1994, 35, 2121; F.A. Davis, J. Szewczyk and R.E. Reddy, J. Org. Chem., 1996, 61, 2222; T. Fujisawa, Y. Kooriyama and M. Shimizu, Tetrahedron Lett., 1996, 37, 3881; F.A. Davis and R.E. Reddy, Tetrahedron: Asymmetry, 1994, 5, 955.
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M. Mikalajczyk, P. Lyzwa, J. Drabowicz, M.W. Wieczorek and J. Blaszczyk, Chem. Commun., 1996, 1503; I.M. Lefebvre and S.A. Evans, J. Org. Chem., 1997, 62, 7532.
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M. Mikalajczyk, P. Lyzwa, J. Drabowicz, M.W. Wieczorek and J. Blaszczyk, Chem. Commun., 1996, 1503; I.M. Lefebvre and S.A. Evans, J. Org. Chem., 1997, 62, 7532.
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note
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Using complete optimizations at MP2/6-31 +G* level, 1r3 and 1tsr3 could not be located on the PE surface. All attempts to locate these structures using the Eigenvalue Following (EF) procedures also failed to find them. Finally as shown in Fig. 2, partial optimization with constrained CNSO dihedral angles also failed to show any minimum corresponding to 1r3.
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0010920822
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note
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The calculations at HF/6-31 +G*, B3LYP/6-31 + G* and MP2/6-31 + G* levels did not lead to any such stationary point. This may be a limitation of the optimization procedure. The important geometric parameters of 1tsi obtained at the HF/6-31G* level are C-N 1.232, N-S 1.607, S-O 1.458 Å, N-S-O 114.7°, C-N-S 180.05°, C-N-S-O 138.0° and C-N-S-H 246.9°. Normal mode analysis of the negative frequency of 1tsi (at HF/6-31G* level) and 2tsi (at HF/ 6-31G*level) showed vibration corresponding to N-inversion and C=N rotation.
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67
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0010858148
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note
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The structural features of 2tsi do appear to connect 2E and 2Z. We have tried to locate other possible structures of 2tsi. All other apparently possible structures converged to 2tsi on complete optimization.
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