-
2
-
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21844437339
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For reviews concerning the synthesis of piperidines, see:
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For reviews concerning the synthesis of piperidines, see:. Bailey P.D., Millwood P.A., and Smith P.D. Chem. Commun. (1998) 633
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11
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70350447783
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Schopf C., Kauffmann T., Berth P., Bundshuh W., Dummer G., Fett H., Habermehl G., Wieters E., and Wust W. Liebigs Ann. Chem. (1959) 134
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15
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4744346531
-
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For selected applications of this transformation in natural product synthesis from this laboratory, see:
-
For selected applications of this transformation in natural product synthesis from this laboratory, see:. Davies S.G., Haggitt J.R., Ichihara O., Kelly R.J., Leech M.A., Price Mortimer A.J., Roberts P.M., and Smith A.D. Org. Biomol. Chem. 2 (2004) 2630
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16
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42349103981
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17
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42349111665
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Abraham E., Brock E.A., Candela-Lena J.I., Davies S.G., Georgiou M., Nicholson R.L., Perkins J.H., Roberts P.M., Russell A.J., Sánchez-Fernández E.M., Scott P.M., Smith A.D., and Thomson J.E. Org. Biomol. Chem. 6 (2008) 1665
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Davies S.G., Iwamoto K., Smethurst C.A.P., Smith A.D., and Rodriguez-Solla H. Synlett (2002) 1146
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Davies, S.G.1
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25
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0037471537
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Chippindale A.M., Davies S.G., Iwamoto K., Parkin R.M., Smethurst C.A.P., Smith A.D., and Rodriguez-Solla H. Tetrahedron 59 (2003) 3253
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26
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0030987385
-
-
3 proved to be an effective and operationally simple procedure for the preparation of (R)-N-but-3-enyl-N-(α-methylbenzyl)amine on multigram scale. Deprotonation of (R)-N-but-3-enyl-N-(α-methylbenzyl)amine in THF at -78 °C using BuLi gave a pale yellow solution of the requisite lithium amide
-
3 proved to be an effective and operationally simple procedure for the preparation of (R)-N-but-3-enyl-N-(α-methylbenzyl)amine on multigram scale. Deprotonation of (R)-N-but-3-enyl-N-(α-methylbenzyl)amine in THF at -78 °C using BuLi gave a pale yellow solution of the requisite lithium amide
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Karoyan, P.1
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27
-
-
70350438380
-
-
note
-
1H NMR spectrum of both the crude reaction mixture and the pure product.
-
-
-
-
28
-
-
0000453565
-
-
For examples of the analogous γ-deprotonation of enones and kinetic reprotonation, see:
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For examples of the analogous γ-deprotonation of enones and kinetic reprotonation, see:. Rathke M.W., and Sullivan D. Tetrahedron Lett. 13 (1972) 4249
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Rathke, M.W.1
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0001661322
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Alcock S.G., Baldwin J.E., Bohlmann R., Harwood L.M., and Seeman J.I. J. Org. Chem. 50 (1985) 3526
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Alcock, S.G.1
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Guha S.K., Shibayama A., Abe D., Sakaguchi M., Ukaji Y., and Inomata K. Bull. Chem. Soc. Jpn. 77 (2004) 2147
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43
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70350455879
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-
note
-
Full details are contained in the ESI.
-
-
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45
-
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59949097919
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Claridge T.D.W., Davies S.G., Lee J.A., Nicholson R.L., Roberts P.M., Russell A.J., Smith A.D., and Toms S.M. Org. Lett. 10 (2008) 5437
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0043192317
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Angoli, M.1
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48
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Heydenreich M., Koch A., Lazar L., Szatmari I., Sillanpaa R., Kleinpeter E., and Fulop F. Tetrahedron 59 (2003) 1951
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16444367832
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34247553192
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Al-Sarabi, A.E.1
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63
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53849126527
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Krishnan S., Bagdanoff J.T., Ebner D.C., Ramtohul Y.K., Tambar U.K., and Stoltz B.M. J. Am. Chem. Soc. 130 (2008) 13745
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64
-
-
70350436255
-
-
note
-
Reduction with L-Selectride resulted in a 76:24 mixture of diastereoisomers.
-
-
-
-
65
-
-
0344391929
-
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Angoli M., Barilli A., Lesma G., Passarella D., Riva S., Silvani A., and Danieli B. J. Org. Chem. 68 (2003) 9525
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Danieli, B.7
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66
-
-
22044440895
-
-
A similar transition state was proposed by Pasarella et al. to rationalise the high levels of selectivity observed upon the substrate directed addition of the reagent derived from diethylzinc and (-)-ephedrine to [N(1′)-tert-butoxycarbonylpiperidin-2′-yl]ethanal; see:
-
A similar transition state was proposed by Pasarella et al. to rationalise the high levels of selectivity observed upon the substrate directed addition of the reagent derived from diethylzinc and (-)-ephedrine to [N(1′)-tert-butoxycarbonylpiperidin-2′-yl]ethanal; see:. Passarella D., Barilli A., Belinghieri F., Fassi P., Riva S., Sacchetti A., Silvani A., and Danieli B. Tetrahedron: Asymmetry 16 (2005) 2225
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Passarella, D.1
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Sacchetti, A.6
Silvani, A.7
Danieli, B.8
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67
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84987366652
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Schopf C., Gams E., Koppernock F., Raush R., and Wallbe R. Liebigs Ann. Chem. 732 (1970) 181
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Schopf, C.1
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69
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84982066233
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Schopf C., Bundshuh W., Dummer G., Kauffmann T., and Kress R. Liebigs Ann. Chem. 628 (1959) 101
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Schopf, C.1
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72
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-
33845282438
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Corey E.J., Bakshi R.K., Shibata S., Chen C.-P., and Singh V.K. J. Am. Chem. Soc. 109 (1987) 7925
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Corey, E.J.1
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74
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0021775497
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Masamune S., Choy W., Petersen J.S., and Sita L.R. Angew. Chem., Int. Ed. Engl. 24 (1985) 1
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Masamune, S.1
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-
79
-
-
70350434069
-
-
note
-
The optical rotations of pyrrolsedamine and allopyrrolsedamine have not been reported; the absolute configurations of the natural products therefore remain unknown.
-
-
-
-
80
-
-
5244370033
-
-
Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Organometallics 15 (1996) 1518
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Pangborn, A.B.1
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Rosen, R.K.4
Timmers, F.J.5
-
81
-
-
70350462539
-
-
note
-
+) requires 227.2011; found 227.2003.
-
-
-
-
82
-
-
0034595783
-
-
Baezinger M., Gobbi L., Riss B.P., Schaefer F., and Vaupel A. Tetrahedron: Asymmetry 11 (2000) 2231
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Baezinger, M.1
Gobbi, L.2
Riss, B.P.3
Schaefer, F.4
Vaupel, A.5
-
83
-
-
70350457913
-
-
note
-
A fraction containing both double bond isomers was also obtained (538 mg, 5%).
-
-
-
-
86
-
-
70350443374
-
-
note
-
+) requires 241.2168; found 241.2173.
-
-
-
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