Coordinative unsaturation in chiral organolanthanides. synthetic and asymmetric catalytic mechanistic study of organoyttrium and -lutetium complexes having pseudo-meso Me2Si(η5-RC5H3)(η 5-R*C5H3) ancillary ligation

Organometallics

Volumn 15, Issue 7, 1996, Pages 1765-1784

  Haar, Christopher M ^a   Stern, Charlotte L ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; HYDROGENATION; LUTETIUM COMPOUNDS; MOLECULAR STRUCTURE; OLEFINS; ORGANIC COMPOUNDS; ORGANOMETALLICS;

ANCILLARY LIGATION; CYCLIZATION; ENANTIOSELECTIVITIES; ORGANOLANTHANIDES; ORGANOLUTETIUM COMPLEXES; ORGANOYTTRIUM COMPLEXES;

YTTRIUM COMPOUNDS;

EID: 0030562964     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950871v     Document Type: Article

References (192)

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118. (b) Anomalous dispersion, pp 234-237.
119. (c) Absorption, pp 204-205.
120. (d) Extinction, pp. 409-412.
121. (e) Patterson function; see Fourier synthesis and pp 270-288.
122. (f) Direct methods, pp 315-338.
123. (g) Vector methods, pp 339-349.
124. (h) Fourier synthesis, pp 222-226, 246-262, 353-362, 381, 445-448.
125. (i) Least squares, pp 385-394, 395-397, 405-406, 454-458.
126. (j) Structure factors, pp 217-222, 230-246, 262.
127. International Tables for X-Ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch Press: Birmingham, 1974; Vol. IV:
128. (a) Mass attenuation coefficients, pp 61-66.
129. (b) Analytical approximation to the scattering factors, pp 99-101.
130. (c) Anomalous dispersion corrections, pp 149-150.
131. The crystal was assumed to be a convex polyhedron bound by plane surfaces, i.e., the crystal faces. A numerical integration of the beam path length was carried out over the entire volume of the sample to evaluate the transmission coefficient for each reflection. For a complete description see: Busing, W. R.; Levy, H. A. Acta Crystallogr. 1957, 10, 180.
132. Calculations were performed on a DEC VAX 11/750 computer system.
133. (a) Elsenbaumer, R. L; Mosher, H. S. J. Org. Chem. 1979, 44, 600-604.
134. (b) Lardicci, L.; Menicagli, R.; Salvadori, P. Gazz. Chim. Ital. 1968, 98, 738-759.
135. (c) Streitwieser, A.; Granger, M. R. J. Org. Chem. 1967, 32, 1528-1529.
136. Lee, H.-J.; Wilson, I. B. Biochim. Biophys. Acta 1971, 242, 519.
137. (a) Bruno, J. W.; Marks, T. J.; Morss, L. R. J. Am. Chem. Soc. 1993, 105, 6824.
138. (b) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. In Bonding Energetics in Organometallic Compounds; Marks, T. J., Ed.; ACS Symposium Series 428; American Chemical Society Washington, DC, 1990; p 159.
139. (c) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844.
140. (d) Ziegler, T.; Tschinke, V.; Versluis, L.; Baerends, E. J.; Ravenek, W. Polyhedron 1988, 7, 1625.
141. (e) Schock L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701.
142. (f) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1987, 109, 7979.
143. (g) Bruno, J. W.; Stecher, H. A.; Morss, L. R.; Sonnenberger, D. C.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 7275.
144. (h) Sonnenberger, D. C.; Morss, L. R.; Marks, T. J. Organometallics 1985, 4, 352.
145. Denninger, U. E.; Marks, T. J. Manuscript in preparation.
146. (a) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114-12129.
147. (b) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3326-3327.
148. (a) Schumann, H.; Albrecht, I.; Loebel, J.; Hahn, E.; Hossain, M. B.; Van der Helm, D. Organometallics 1986, 5, 1296-1304.
149. (b) Rausch, M. D.; Moriarty, K. J.; Atwood, J. L.; Weeks, J. A.; Hunter, W. E.; Brittain, H. G. Organometallics 1986, 5, 1281-1283.
150. (c) Watson, P. L.; Whitney, J. F.; Harlow, R. L. Inorg. Chem. 1981, 20, 3271-3278.
151. (d) Tilley, T. D.; Andersen, R. A. Inorg. Chem. 1981, 20, 3267-3271.
152. (e) Wayda, A. L.; Evans, W. E. Inorg. Chem. 1980, 19, 2190-2191.
153. (a) Lappert, M. F.; Singh, A.; Atwood, J. L.; Hunter, W. E.; Zhang, H. M. J. Chem. Soc., Chem. Commun. 1983, 69-70.
154. (b) Lappert, M. F.; Singh, A.; Atwood, J. L.; Hunter, W. E. J. Chem. Soc., Chem. Commun. 1981, 1191-1192.
155. (c) Atwood, J. L.; Hunter, W. E.; Rogers, R. D.; Holton, J.; McMeeking, J.; Pearce, R.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1978, 140-142.
156. Piemontesi, F.; Camurati, E.; Resconi, L.; Balboni, D.; Sironi, A.; Moret, M.; Ziegler, R.; Piccolrovazzi, N. Organometallics 1995, 14, 1256.
157. Shannon, R. E. Acta Crytallogr. 1976, A32, 751-760.
158. (a) Lappert, M. F.; Riley, P. I.; Yarrow, P. I. W.; Atwood, J. L.; Hunter, W. E.; Zaworotko, M. J. J. Chem. Soc., Dalton Trans. 1981, 814-821.
159. (b) Jeffery, J.; Lappert, M. J.; Luong-Thi, N. T.; Atwood, J. L.; Hunter, W. E. J. Chem. Soc., Chem. Commun. 1978, 1081-1083.
160. 3+ ion, only 6 cyclopentadienyl resonances are observed over the range 25-90 °C: Haar, C. M.; Marks, T. J. Unpublished observations.
161. (a) Schock, L. E.; Brock, C. P.; Marks, T. J. Organometallics 1987, 6, 232.
162. (b) McDade, C.; Brock, C. P.; Bercaw, J. E. Organometallics 1982, 1, 1629.
163. (a) Bakos, J.; Tóth, I.; Heil, B.; Markó, L. J. Organomet. Chem. 1985, 279, 23-29.
164. (b) Hayashi, T.; Tanaka, M.; Ogata, I. Tetrahedron Lett. 1977, 18, 295-296.
165. Segel, I. H. Enzyme Kinetics; Wiley: New York, 1975; Chapters 2, 9.
166. Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1987, 109, 7979-7985 and references within.
167. (a) Eisen, M. S.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 10358-10368.
168. (b) Gillespie, R. D.; Burwell, R. J.; Marks, T. J. Langmuir 1990, 6, 1465-1477.
169. (a) Fendrick, C. M.; Schertz, L. D.; Day, V. W.; Marks, T. J. Organometallics 1988, 7, 1828-1830.
170. (b) Fendrick, C. M.; Mintz, E. A.; Schertz, L. D.; Marks, T. J.; Day, V. W. Organometallics 1984, 3, 819-821.
171. 12,13,16,25,29 (a) Holton, J.; Lappert, M. F.; Ballard, D. G. H.; Atwood, J. L., Hunter, W. E. J. Chem. Soc., Dalton Trans. 1979, 54-60. (b) Holton, J.; Lappert, M. F.; Scollary, G. R.; Ballard, D. G. H.; Pearce, R.; Atwood, J. L.; Hunter, W. E. J. Chem. Soc., Chem. Commun. 1976, 425-426.
172. 12,13,16,25,29 (a) Holton, J.; Lappert, M. F.; Ballard, D. G. H.; Atwood, J. L., Hunter, W. E. J. Chem. Soc., Dalton Trans. 1979, 54-60. (b) Holton, J.; Lappert, M. F.; Scollary, G. R.; Ballard, D. G. H.; Pearce, R.; Atwood, J. L.; Hunter, W. E. J. Chem. Soc., Chem. Commun. 1976, 425-426.
173. (a) Ozawa, F.; Park, J. W.; Mackenzie, P. B.; Schaefer, W. P.; Henling, L. M.; Grubbs, R. H. J. Am. Chem. Soc. 1989, 111, 1319-1327.
174. (b) Busch, M. A.; Harlow, R.; Watson, P. L. Inorg. Chim. Acta 1987, 140, 15-20.
175. (c) Waymouth, R. M.; Santarsiero, B. D.; Coots, R. J.; Bronikowski, M. J.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 1427-1441.
176. (d) Holton, J.; Lappert, M. F.; Pierce, R.; Yarrow, P. I. W. Chem. Rev. 1983, 83, 135-201.
177. (e) Berry, R. S. J. Chem. Phys. 1960, 32, 933-938.
178. (a) Wardell, J. L. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 2.
179. (b) Fraenkel, G.; Beckenbaugh, W. E.; Yang, P. P. J. Am. Chem. Soc. 1976, 98, 6878-6885.
180. (c) Witanowski, M.; Roberts, J. D. J. Am. Chem. Soc. 1966, 88, 737-741.
181. (d) Whitesides, G. M.; Witanowski, M.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 2854-2862.
182. (a) Schleyer, P. v. R.; Tidor, B.; Jemmis, E. D.; Chandrasekhar, J.; Würthein, E. U.; Kos, A. J.; Luke, B. T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 484-488.
183. (b) Jemmis, E. D.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 527-533.
184. (c) Clark, T.; Schleyer, P. v. R.; Pople, J. A. J. Chem. Soc., Chem. Commun. 1978, 137-138.
185. Evans, W. J.; Ulibarri, T. A.; Ziller, J. W. J. Am. Chem. Soc. 1890, 112, 219-223.
186. 21a (64) (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, No. 428, 159-174 and references therein. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853 and references therein.
187. 21a (64) (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, No. 428, 159-174 and references therein. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853 and references therein.
188. (a) Nolan, S. P.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 8538-8540.
189. (b) Casey, C. P.; Hallenbeck, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770-9771.
190. (c) Jordan, R. F.; Wu, Z.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867-5868.
191. Reference 1h, Chapter 1.
192. Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515-5525 and references therein.