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Stannyldienoic esters: (a) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.
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Hosoya, T.; Sumi, K.; Doi, H.; Wakao, M.; Suzuki, M. Org. Biomol. Chem 2006, 4, 410-415. See also refs 3b, d.
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(n) Hosoya, T.; Sumi, K.; Doi, H.; Wakao, M.; Suzuki, M. Org. Biomol. Chem 2006, 4, 410-415. See also refs 3b, d.
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34
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(c) Rojas, C. M. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; John Wiley & Sons: Hoboken, NJ, 2005; pp 355-374.
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(a) Kearney, A. M.; Vanderwal, C. D. Angew. Chem., Int. Ed. 2006, 45, 7803-7806.
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49349133364
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The regioselectivity of addition of trimethylstannyllithium to enones has been studied: Still, W. C.; Mitra, A. Tetrahedron Lett. 1978, 19, 2659-2662.
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The regioselectivity of addition of trimethylstannyllithium to enones has been studied: Still, W. C.; Mitra, A. Tetrahedron Lett. 1978, 19, 2659-2662.
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40
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37049091415
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The conjugate addition of tin anions and stannylcopper reagents, in particular, is well documented. For examples, some of which include conjugate addition/elimination reactions to generate vinylstannanes from acceptors that bear excellent β-leaving groups, see: (a) Piers, E.; Morton, H. E. J. Chem. Soc., Chem. Commun. 1978, 1033-1034.
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The conjugate addition of tin anions and stannylcopper reagents, in particular, is well documented. For examples, some of which include conjugate addition/elimination reactions to generate vinylstannanes from acceptors that bear excellent β-leaving groups, see: (a) Piers, E.; Morton, H. E. J. Chem. Soc., Chem. Commun. 1978, 1033-1034.
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42
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0001469504
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(c) Piers, E.; Chong, J. M.; Morton, H. E. Tetrahedron Lett. 1981, 22, 4905-4908.
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Piers, E.1
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Imanieh, H.1
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Davies, G.M.5
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45
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60949083812
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2SiLi with simple vinylogous amides. In one particular case, these authors found that the inclusion of an activated alkyl halide was required for successful outcomes, but this observation was not attributed to the reversibility of the process, nor was a satisfying explanation found. See: Fleming, I.; Marangon, E.; Roni, C.; Russell. M. G.; Taliansky Chamudis, S. Can. J. Chem. 2004, 82, 325-332.
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2SiLi with simple vinylogous amides. In one particular case, these authors found that the inclusion of an activated alkyl halide was required for successful outcomes, but this observation was not attributed to the reversibility of the process, nor was a satisfying explanation found. See: Fleming, I.; Marangon, E.; Roni, C.; Russell. M. G.; Taliansky Chamudis, S. Can. J. Chem. 2004, 82, 325-332.
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46
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0006625539
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For the reversibility of trialkylstannyl anion additions to unsaturated electrophiles, see: Cox, S. D.; Wudl, F. Organometallics 1983, 2, 184-185. See also ref 8.
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For the reversibility of trialkylstannyl anion additions to unsaturated electrophiles, see: Cox, S. D.; Wudl, F. Organometallics 1983, 2, 184-185. See also ref 8.
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47
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33750437727
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ε-Vinylstannane 18 has only been made stereoselectively once, via a multistep sequence: Asano, M.; Inoue, M.; Watanabe, K.; Abe, H.; Katoh, T. J. Org. Chem. 2006, 71, 6942-6951.
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ε-Vinylstannane 18 has only been made stereoselectively once, via a multistep sequence: Asano, M.; Inoue, M.; Watanabe, K.; Abe, H.; Katoh, T. J. Org. Chem. 2006, 71, 6942-6951.
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48
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0001739233
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Stannane 20 is most frequently made by Lewis acid mediated acetylation of trans-1,2-bis(tributylstannyi)ethylene: (a) Peel, M. R.; Johnson, C. R. Tetrahedron Lett. 1986, 27, 5947-5950.
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Stannane 20 is most frequently made by Lewis acid mediated acetylation of trans-1,2-bis(tributylstannyi)ethylene: (a) Peel, M. R.; Johnson, C. R. Tetrahedron Lett. 1986, 27, 5947-5950.
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49
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0011906205
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It has been used in synthesis several times; for representative examples, see: (b) Johnson, C. R, Kadow, J. F. J. Org. Chem. 1987, 52, 1493-1500
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It has been used in synthesis several times; for representative examples, see: (b) Johnson, C. R.; Kadow, J. F. J. Org. Chem. 1987, 52, 1493-1500.
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50
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0000330268
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(c) Echavarren, A. M.; Pérez, M.; Castańo, A. M.; Cuerva, J. M. J. Org. Chem. 1994, 59, 4179-4185.
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Echavarren, A.M.1
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51
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0030446694
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(d) Winkler, J. D.; Holland, J. M.; Peters, D. A. J. Org. Chem. 1996, 61, 9074-9075.
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Winkler, J.D.1
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52
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33947480951
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a of trialkylstannanes, see: (a) Gilman, H.; Marrs, O. L.; Trepka, W. J.; Diehl, J. W. J. Org. Chem. 1962, 27, 1260-1265.
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a of trialkylstannanes, see: (a) Gilman, H.; Marrs, O. L.; Trepka, W. J.; Diehl, J. W. J. Org. Chem. 1962, 27, 1260-1265.
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54
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84982341931
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Vinylogous amides from ketones and amide acetals: Meerwein, H.; Florian, W.; Schon, G.; Stopp, G. Liebigs Ann. Chem. 1961, 641, 1-39.
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Vinylogous amides from ketones and amide acetals: Meerwein, H.; Florian, W.; Schon, G.; Stopp, G. Liebigs Ann. Chem. 1961, 641, 1-39.
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55
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60949097589
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Tendency of ketone-derived vinylogous amides related to 23 to undergo conjugate addition/elimination with alkyllithium nucleophiles: Abdullah, R. F.; Fuhr, K. H. J. Org. Chem. 1978, 43, 4248-4250.
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Tendency of ketone-derived vinylogous amides related to 23 to undergo conjugate addition/elimination with alkyllithium nucleophiles: Abdullah, R. F.; Fuhr, K. H. J. Org. Chem. 1978, 43, 4248-4250.
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56
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84922377851
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Stannane 24 has been prepared by conjugate addition/elimination of the relevant β-iodoenone: Piers, E.; Morton, H. E.; Chong, J. M. Can. J. Chem. 1987, 65, 78-87.
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Stannane 24 has been prepared by conjugate addition/elimination of the relevant β-iodoenone: Piers, E.; Morton, H. E.; Chong, J. M. Can. J. Chem. 1987, 65, 78-87.
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59
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60949095239
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The conditions in Scheme 4 were derived from those detailed in ref 18b.
-
The conditions in Scheme 4 were derived from those detailed in ref 18b.
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60
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60949110094
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While stannyldienals with substituents α to the aldehyde such as 10 and 14 (and presumably 16) generally cross-couple with retention of alkene geometries, stannane 12 readily isomerizes under Stille conditions, affording a mixture of product geometrical isomers. The inclusion of stoichiometric NEt3 suppressed isomerization in the synthesis of 26. A similar isomerization of the Z-isomer of 18 to the Ε-isomer under Stille conditions has been reported; see ref 18a
-
3 suppressed isomerization in the synthesis of 26. A similar isomerization of the Z-isomer of 18 to the Ε-isomer under Stille conditions has been reported; see ref 18a.
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