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Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 4-646. For a recent report on the short lifetime of α-silyl radicals, see: Le Gall, E.; Hurvois, J.-P.; Sinbandhit, S. Eur. J. Org. Chem. 1999, 2645, 5-2653.
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0000782213
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25
-
-
84872269899
-
-
note
-
Strong support for this stereochemical assignment comes from the presence of a large 1,2-diaxial coupling between the adjacent bridgehead and silyl-substituted methines in the proton NMR spectrum.
-
-
-
-
26
-
-
0035543974
-
-
(a) Clark, J. S.; Hodgson, P. B.; Goldsmith, M. D.; Blake, A. J.; Cooke, P. A.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 2001, 3325-3337.
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Cooke, P.A.5
Street, L.J.6
-
28
-
-
84872274001
-
-
note
-
Retention was calculated as % ee of quinolizidines 4a (71%), 5a (63%), or 5b (77%) divided by % ee of 3a or 3b (both 85%).
-
-
-
-
29
-
-
84872263787
-
-
note
-
iPrOH/hex and a flow rate of 0.5 mL/min.
-
-
-
-
30
-
-
84872273152
-
-
note
-
Alkylation product 3b was found to decompose slowly under the conditions of its formation, requiring that the reaction be stopped prior to complete consumption of starting material. The same problem, though less severe, was encountered in the alkylation of 3a.
-
-
-
-
31
-
-
84872273480
-
-
note
-
25NOSi: C, 71.03; H, 8.77; N, 4.87. Found: C. 71.0; H, 8.93; N, 4.52.
-
-
-
-
32
-
-
84872268719
-
-
note
-
Reduction with L-selectride or under Meerwein-Pondorff-Verley conditions also gave 6b exclusively, but in slightly lower yield.
-
-
-
-
33
-
-
84872270693
-
-
note
-
2D NOESY NMR data clearly indicated the expected axial alcohol resulting from equatorial attack of the bulky hydride reagent.
-
-
-
-
35
-
-
84872272205
-
-
note
-
3), indicating a small degradation in optical purity of 4b during the subsequent manipulations.
-
-
-
-
36
-
-
0001399740
-
-
Marquant, A. L.; Podlogar, B. L.; Huber, E. W.; Demeter, D. A.; Peet, N. P.; Weintraub, H. J. R.; Angelastro, M. R. J. Org. Chem. 1994, 59, 2092-2100.
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Peet, N.P.5
Weintraub, H.J.R.6
Angelastro, M.R.7
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38
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84872275949
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(b) Overkleeft, H. S.; Bruggeman, P.; Pandit, U. K. Tetrahedron Lett. 1998, 39, 3896-3872.
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39
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0342940774
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(c) Carretero, J. C.; Arrrayas, R. G.; De Garcia, I. S. Tetrahedron Lett. 1997, 38, 8537-8540.
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Carretero, J.C.1
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