Derivatives of 2-amino-2′-diphenylphosphino-1,1′-binaphthyl (MAP) and their application in asymmetric palladium(O) -catalyzed allylic substitution

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7738-7748

  Vyskočil, Štěpán ^a,c   Smrčina, Martin ^b   Hanuš, Vladimir ^a   Polášek, Miroslav ^b   Kočovský, Pavel ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002017795     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980757x     Document Type: Article

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182. (f) Vyskocil, S.; Smrcina, M.; Hanus, V; Polâsek, M.; Kocovsky, P. Chem. Commun. 1998, 585.
183. (a) Smrcina, M.; Vyskocil, S.; Poli'vkovâ, J.; Polâkovâ, J.; Sejbal, J.; Hanus, V.; Polâsek, M.; Verrier, H.; Kocovsky, P. Tetrahedron: Asymmetry 1997, 8, 537.
184. (b) Vyskocil, S.; Jaracz, S.; Smrcina, M.; Stfcha, M.; Hanus, V; Polâsek, M.; Kocovsky P. J. Org. Chem. 1998, 63, adjacent paper.
185. 2O (rt, 8 h), followed by Zemplén hydrolysis of the OAc group (dry MeOH, cat. sodium) improved the overall yield of the "monoacetate" (R)-16 to 95%.
186. Unlike for (R)-5, attempted alkylation with 2-adamantanone failed, demonstrating the steric limitations of this protocol:
187. (a) Brown, K. J.; Berry, M. S.; Waterman, K. C.; Lingenfelter, D.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 706, 4717. For a recent application of an analogous naphthalene-derived palladacycle, see:
188. (b) Gladialli, S.; Pilacchini, S.; Fabbri, D.; Menassero, M.; Sansoni, M. Tetrahedron: Asymmetry 1998, 9, 391.
189. Zhang, X.; Masima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
190. Note that the few binaphthyl ligands of the P,N-type, previously employed in the Pd(0)-catalyzed allylic substitution,1911-27-3013 did not have the ligating groups directly connected with the aromatic system.
191. The absolute configuration of 28 has previously been established via a chemical correlation of its (S)-(-)-enantiomer with (S)-(+)-2-' phenylsuccinate: Trost, B. M.; Murphy, D. J. Organomelallics 1985, 4, 1143.
192. Interestingly, the absolute configuration of 29 has never been rigorously established. Authors, who prepared this compound via the Pd(0)-catalyzed allylic substitution,17'21'39 have arbitrarily assigned its configuration in analogy to 28; we thank Professors Trost and Williams for this personal communication. We have now confirmed the assignment by chemical correlation: methylation of the sodium salt of (S)(-)-28 with CH3I afforded (R)-(+)-29. Note the pseudoinversion of configuration of 29 vs 28 due to the change in the substituent priorities.
193. The absolute configuration of 30 has been established previously via a chemical correlation with (fl)-(+)-28, which was converted into (S)-(-)-30 in three steps.27'
194. Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347.
195. 44'43 whereas the recent source claims that the (R,E) isomer is levorotatory,44 this configuration was assigned to the dextrorotatory enantiomer in an earlier paper, based on an extensive correlation with several compounds of known configuration.43 Unfortunately, we have not been able to communicate with the senior author of the recent paper. As a result, the assignment of (S) configuration to (-)-32 indicated in Schemes 5 and 7 has to be treated as tentative (and very likely) but not rigorously proven.
196. McKew, J. C.; Kurth, M. J. J. Org. Chem. 1993, 58, 4589.
197. Hill, R. K; Soman, R.; Sawada, S. J. Org. Chem. 1972,37,3737.
198. Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 720, 1681.
199. For the original reports on the "memory effect" in the Pd(0)catalyzed allylic substitution, see: (a) Fiaud, J. C.; Malleron, J. L. Tetrahedron. Lett. 1981, 22, 1399.
200. (b) Trost, B. M.; Schmuff, N. R. Tetrahedron Lett. 1981,22, 2999.
201. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996,118,235. For the most recent insight, see:
202. LloydJones, G. C.; Stephen, S. C. Chem.-Eur. J., in press.
203. Hayashi, T.; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561.
204. An even higher ratio favoring the branched isomer (5:95) was found for the analogous substrate possessing 1-naphthyl in place of phenyl.19h
205. The enantiomeric excess has not been determined for either 36a or 36b in view of the very low yield.
206. 2-complex jn question was generated by a stoichiometric reaction of dimethyl sodiomalonate with the (,-rcyclohexenyl)Pd(2) complex and found to be stable at room temperature for several days.
207. + as follows: (a) Pathak, D. D.; Adams, H.; Bailey, N. A.; King, P. J.; White, C. J. Organomet. Chem. 1994,479, 237.
208. (b) Feiken, N.; Pregosin, P. S.; Trabesinger, G. Organometallics 1997,16, 537.
209. Feiken, N.; Pregosin, P. S.; Trabesinger, G. Organometallics 1998, 17, 5756. For an overview, see:
210. Pregosin, P. S.; Trabesinger, G. J. Chem. Soc., Dalton Trans. 1998, 727.
211. Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998,120, 459.
212. 46 this effect can now also be viewed as originating from the coordination of Ni to the aromatic naphthyl nucleus rather than to the MeO group. Application of MAP to hydrovinylation would certainly be interesting as it may shed more light on this mechanistic issue.