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Crich, D.; Pastrana-Grass, I.; Quintero-Cortes, L.; Sandoval-Ramirez, J. Heterocycles 1994, 38, 719-724.
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16
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0028859348
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23
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0011167360
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Hino, T.1
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24
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0001226535
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0000373193
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Barton, D.H.R.1
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30
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2442637109
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note
-
The absolute configuration for chiral C-atoms was unambiguously determined as 2R,3aS,8aS and the carbamate partial double bond is reflected in the short distance N1-C9, 1.369(4) Å.
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31
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85087606111
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note
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2Ph moiety along the N8-S1 bond. On the other hand, the formation of a double bond during the ring opening is confirmed by bond lengths C3a-C8a = 1.333(6) and 1.345(6) Å for the first and second molecule, respectively.
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32
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2442655974
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note
-
The cyano group is characterized by a formal triple bond, C13-N14 = 1. 127 (5) Å; the configuration for C3a and C8a remains unchanged relative to starting material, while the C2 atom presents now an S configuration.
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33
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37049074298
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Chan, C.-O.; Cooksey, C. J.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 777-780.
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Chan, C.-O.1
Cooksey, C.J.2
Crich, D.3
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34
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2442647143
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note
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36 pyrrolidine derived iminium ions, neighboring group participation from the carbamoyl or sulfonyl group has been invoked as a possible explanation for the stereoselectivity. While this may be possible with the N-sufonyl system, with the tetrahedral sulfur and longer N-S and S-O bonds, it seems unlikely in N-carbamoyl systems, such as those described here, when it would require the disruption of the crystallographically well-established N=C(O-)OMe double bond character.
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36
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0033575451
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Ungureanu, I.; Bologa, C.; Chayer, S.; Mann, A. Tetrahedron Lett. 1999, 40, 5315-5318.
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Ungureanu, I.1
Bologa, C.2
Chayer, S.3
Mann, A.4
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