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For reviews, see: (a) de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21b, pp 1953-2009.
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De Koning, H.1
Speckamp, W.N.2
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For recent examples, see: (a) Zhang, J.; Wei, C.; Li, C.-J. Tetrahedron Lett. 2002. 43, 5731-5733.
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Zhang, J.1
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(b) Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994.
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0035915332
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(c) Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517.
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(b) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois. J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
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Espino, C.G.1
Wehn, P.M.2
Chow, J.3
Du Bois, J.4
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13
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0033550253
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Diazoalkane C-H insertion reactions also occur preferentially at heteroatom-substituted C-H centers, see: (a) Sulikowski, G. A.; Lee, S. Tetrahedron Lett. 1999, 40, 8035-8038. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296-3305 and references thererin.
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Sulikowski, G.A.1
Lee, S.2
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14
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0000705205
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and references thererin
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Diazoalkane C-H insertion reactions also occur preferentially at heteroatom-substituted C-H centers, see: (a) Sulikowski, G. A.; Lee, S. Tetrahedron Lett. 1999, 40, 8035-8038. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296-3305 and references thererin.
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Wang, P.1
Adams, J.2
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15
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0013399957
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note
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2 centers. We have never observed transannular C-H insertion, however, with any cycloalkanol-derived sulfamate.
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-
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16
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0013399958
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note
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2, grade 643 (see the Supporting Information for details).
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17
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0037099190
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Metal-acetylides have been employed in novel, highly selective addition reactions, see: (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. (b) Frantz, D. E.; Fassler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373-381 and references therein.
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Angew. Chem., Int. Ed.
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, pp. 2535-2538
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Koradin, C.1
Polborn, K.2
Knochel, P.3
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18
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0038252959
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and references therein
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Metal-acetylides have been employed in novel, highly selective addition reactions, see: (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. (b) Frantz, D. E.; Fassler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373-381 and references therein.
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(2000)
Acc. Chem. Res.
, vol.33
, pp. 373-381
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Frantz, D.E.1
Fassler, R.2
Tomooka, C.S.3
Carreira, E.M.4
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19
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0000302199
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For a comprehensive review of organozinc chemistry, see: Knochel, P.; Millot. N.; Rodriguez, A. L.; Tucker. C. E. Org. React. 2001, 58, 417-731.
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Org. React.
, vol.58
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Knochel, P.1
Millot, N.2
Rodriguez, A.L.3
Tucker, C.E.4
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20
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0013395609
-
-
note
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1H NMR coupling constant, NOE, and/or X-ray analysis.
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-
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22
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0013399325
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note
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2) pseudoequatorially.
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23
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0001019960
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Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968.
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Org. Lett.
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Atfani, M.1
Wei, L.2
Lubell, W.D.3
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24
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0000512831
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and references therein
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Carretero has reported the synthesis of 10, see: Carretero, J. C.; Arrayás, R. G. J. Org. Chem. 1998, 63. 2993-3005 and references therein.
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J. Org. Chem.
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Carretero, J.C.1
Arrayás, R.G.2
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25
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0013349632
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note
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Details for the X-ray structure of 7 are in the Supporting Information.
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26
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0000171418
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4 has been described previously, see: Okamoto, Y.; Kinoshita, T. Chem. Pharm. Bull. 1981, 29, 1165-1169. In our hands, these conditions proved uniquely effective for this rather unusual transformation.
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(1981)
Chem. Pharm. Bull.
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Okamoto, Y.1
Kinoshita, T.2
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