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2-mediated synthesis, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
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24144490041
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Liu, D.-G.1
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38
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68149085749
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1H NMR, and the er was determined by chiral HPLC of N-Ac derivatives of 3; see the Supporting Information.
-
1H NMR, and the er was determined by chiral HPLC of N-Ac derivatives of 3; see the Supporting Information.
-
-
-
-
39
-
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68149090657
-
-
s, 2S-3a, since the absolute configuration of sulfur was not disturbed during the reaction.
-
s, 2S-3a, since the absolute configuration of sulfur was not disturbed during the reaction.
-
-
-
-
40
-
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68149086815
-
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For recent studies on the role of HMPA, see: a
-
For recent studies on the role of HMPA, see: (a) Faran, H.; Hoz, S. Org. Lett. 2008, 70, 865.
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Faran, H.1
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44949129108
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(b) Sadasivam, D. V.; Antharjanam, P. K. S.; Prasad, E.; Flowers, R. A. J. Am. Chem. Soc. 2008, 130, 7228.
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8744311540
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45
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24644499004
-
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The S-O bond and the nitrogen lone pair of electrons should be anti-periplanar; see: a
-
The S-O bond and the nitrogen lone pair of electrons should be anti-periplanar; see: (a) Ferreira, F.; Audouin, M.; Chemla, F. Chem,-Eur. J. 2005, 77, 5269.
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Chem,-Eur. J
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0033993072
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Bharatam, P.V.1
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Amita3
Kaur, D.4
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48
-
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85022594998
-
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Reversibility of carbonyl reduction: (a) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Reversibility of ring formation:
-
Reversibility of carbonyl reduction: (a) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943. Reversibility of ring formation:
-
-
-
-
50
-
-
68149140528
-
-
The tolerance of the R-sulfinyl gauche-interaction in this reaction could be due to the fact that an N-radical might be roughly triagonal (sp 2, similar to its imime precursor; while for polar 1,2-addition to sulfinimines directly yielding a sterically demanding tetrahedral (metallated) N-anion, such R-sulfinyl interaction becomes the determining factor ref 18a, In the latter case, the shift in hybridization state of nitrogen could also affect the conformation of the sulfinyl group
-
2), similar to its imime precursor; while for polar 1,2-addition to sulfinimines directly yielding a sterically demanding tetrahedral (metallated) N-anion, such R-sulfinyl interaction becomes the determining factor (ref 18a). In the latter case, the shift in hybridization state of nitrogen could also affect the conformation of the sulfinyl group.
-
-
-
-
51
-
-
68149109408
-
-
In most polar additions to sulfinimines, coordination of substrate O/N atoms to metal cation was proposed to explain the observed stereoselectivity. If anionic cyclization mechanism predominated in the present case, chelation of the hydroxyl and the sulfinylamino groups to Sm(III) would afford either the cis- products or the opposite sense of chiral induction.
-
In most polar additions to sulfinimines, coordination of substrate O/N atoms to metal cation was proposed to explain the observed stereoselectivity. If anionic cyclization mechanism predominated in the present case, chelation of the hydroxyl and the sulfinylamino groups to Sm(III) would afford either the cis- products or the opposite sense of chiral induction.
-
-
-
-
52
-
-
68149177706
-
-
n occupied the axial orientation as the result of stereoelectronic effects in cyclic systems (ref 17a), and this does not reflect its bulk relative to R in acyclic systems (OSmLn > R>H).
-
n occupied the axial orientation as the result of stereoelectronic effects in cyclic systems (ref 17a), and this does not reflect its bulk relative to R in acyclic systems (OSmLn > R>H).
-
-
-
-
53
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33748668003
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Ianni, J. C; Annamalai, V.; Phuan, P.-W.; Panda, M.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2006, 45, 5502.
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(2006)
Angew. Chem., Int. Ed
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-
Ianni, J.C.1
Annamalai, V.2
Phuan, P.-W.3
Panda, M.4
Kozlowski, M.C.5
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54
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68149129303
-
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Its utility in other asymmetric transformations is being probed
-
Its utility in other asymmetric transformations is being probed.
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