Chiral Lewis acid catalysts in Diels-Alder cycloadditions: Mechanistic aspects and synthetic applications of recent systems

Journal of the Brazilian Chemical Society

Volumn 8, Issue 4, 1997, Pages 289-332

  Dias, Luiz C ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Asymmetric catalysis; Asymmetric Diels Alder cycloaddition reaction; Chiral Lewis acids; Dienophile Lewis acid complex

Indexed keywords

EID: 0031371093     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50531997000400002     Document Type: Review

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140. L-tartrate derived catalysts have been used to effect enantioselective Diels-Alder reaction between α-bromoacrolein and cyclopentadiene: Loh, T.-P.; Wang, R.-B.; Sim, K.-Y. Tetrahedron Lett. 1996, 37, 2989.
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145. It has been demonstrated that 4 Å MS can enhance the enantioselectivities in the Diels-Alder reactions when using only catalytic amounts of Lewis acids: Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
146. (a) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812;
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148. (a) Corey, E.J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289.
149. (b) The Diels-Alder reaction between the more reactive 3-(methylthio)-furan and imide 7 in the presence of catalytic amounts of the chiral titanium catalyst 90, afforded the corresponding cycloadduct in 87%ee with an endo:exo ratio of 85:15: Yamamoto, I.; Narasaka, K. Chem Lett. 1995, 1129.
150. (a) Sarko, C.R.; Haase, C; DiMare, M. J. Org. Chem. 1995, 60, 1777;
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152. (c) In 1996, Seebach and coworkers have published reports dealing with the preparation and the use of polymer-and Dendrimer-Bound Ti-TADOLLates in catalytic enantioselective reactions: Seebach, D.; Marti, R.E.; Hintermann, T. Helv. Chim. Acta. 1996, 79, 1710.
153. (d) See also: Altava, B.; Burguete, M.I.; Escuder, B.; Luis, S.V.; Salvador, R.V.; Fraile, J.M.; Mayoral, J.A.; Royo, A.J. J. Org. Chem. 1997, 62, 3126.
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157. Keck, G.E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
158. Corey found that the tryptophan-derived oxazaborolidine catalyst gave good yields and moderate enantioselectivity for the reaction of Danishefsky's diene and aldehydes via a two step Aldol-Michael sequence. Corey, E.J.; Cywin, C.L.; Roper, T.D. Tetrahedron Lett. 1992, 33, 6907.
159. Wada, E.; Yasuoka, H.; Kanemaza, S. Chem. Lett. 1994, 1637.
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161. (a) Narasaka, K.; Tanaka, H.; Kanai, F. Bull. Chem. Soc. Jpn. 1991, 64, 3871;
162. (b) Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743.
163. (c) Narasaka, K.; Yamamoto, I. Bull. Chem. Soc. Jpn. 1994, 67, 3327.
164. 2 in the equilibrium, decreasing the enantioselectivity of the cycloaddition reaction: Tietze, L.F.; Ott, C.; Frey, U. Liebgs Ann. 1996, 63.
165. (a) Jaquith, J.B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079;
166. (b) Hong, Y.; Kuntz, B.A.; Collins, S. Organometallics 1993, 12, 964.
167. (a) Odenkirk, W.; Bosnich, B. J. Chem. Soc. Chem. Commun. 1995, 1181.
168. (b) For a recent review on enantioselective C-C and C-H bond formation catalyzed by chiral ebthi complexes of titanium and zirconium, see: Hoveyda, A.H.; Morken, J.P. Angew. Chem. Int. Ed. Engl. 1996 35, 1262.
169. For related Diels-Alder reactions using aquo-complexes of ruthenium and titanium, see: (a) Odenkirk, W.; Rheingold, A.L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392; (b) Hollis, T.K.; Robinson, N.P.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 5464.
170. For related Diels-Alder reactions using aquo-complexes of ruthenium and titanium, see: (a) Odenkirk, W.; Rheingold, A.L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392; (b) Hollis, T.K.; Robinson, N.P.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 5464.
171. (a) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967.
172. (b) For a paper describing the importance of chiral activators in the asymmetric catalysis of Diels-Alder reactions by chiral titanium (IV) complexes, see: Matsukawa, S.; Mikami, K. Tetrahedron:Asymmetry 1997, 8, 815.
173. Harada et al. reported that the enantioselectivity in Diels-Alder reactions of acrylates and cyclopentadiene catalyzed by a series of chiral titanium complexes derived from 2, 2′-biaryldiols depend on the biaryl torsional angles: Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron:Asymmetry 1996, 7, 2479.
174. For leading references on the chemistry of bis(oxazolines), see: Denmark, S.E.; Nakajima, N.; Nicaise, O.J.-C.; Faucher, A.-M.; Edwards, J.P. J. Org. Chem. 1995, 60, 4884.
175. Evans, D.A.; Miller, S.J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460.
176. 2+: Otto, S.; Bertoncin, F.; Engberts, J.B.F.N. J. Am. Chem. Soc. 1996, 118, 7702.
177. 2+: Otto, S.; Bertoncin, F.; Engberts, J.B.F.N. J. Am. Chem. Soc. 1996, 118, 7702.
178. Evans, D.A.; Lectka, T.; Miller, S.J. Tetrahedron Lett. 1993, 34, 7027.
179. In 1995, Feringa and coworkers described the utilization of a chiral bis-imine copper (II) complex as catalyst for the Diels-Alder reaction of 1-vinyl-2, 2, 6-trimethyl-cyclohexene and 3-((E)-3-(methoxycarbonyl)-propenoyl)-1, 3-oxazolidin-2-one under high pressure leading to a drimane sesquiterpene precursor in up to 64% ee: Knol, J.; Meetsma, A.; Feringa, B.L. Tetrahedron:Asymmetry 1995, 6, 1069.
180. (a) Evans, D.A.; Murry, J.A.; von Matt, P.; Norcross, R.D.; Miller, S.J. Angew Chem. Int. Ed. Engl. 1995, 34, 798.
181. (b) For a comparative study in catalysis of Diels-Alder and Aldol reactions using cationic bis(oxazoline) and pyridil-bis(oxazoline) Cu(II) and Zn(II) Lewis acids, see: Evans, D.A.; Kozlowski, M.C.; Tedrow, J.S. Tetrahedron Lett. 1996, 37, 7481.
182. (a) Davies, I.W.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. Tetrahedron Lett. 1996, 37, 813.
183. (b) Davies, I.W.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. Tetrahedron Lett. 1996, 37, 1725.
184. (a) Davies, I.W.; Gerena, L.; Castonguay, L.; Senanayake, C.H.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. Chem Commun. 1996, 1753.
185. (b) A similar correlation of ligand bite angle θ and enantioselectivity has been reported by Trost in palladium-catalyzed allylic alkylations: Trost, B.M.; Van Vranken, D.L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
186. (c) See also: Davies, I.W.; Gerena, L.; Lu, N.; Larsen, R.D.; Reider, P.J. J. Org. Chem. 1996, 61, 9629.
187. A more recent publication of the Merck group used a toolbox of bis(oxazoline)-spiroligands to probe the conformational effects in Cu(II)-catalyzed Diels-Alder reactions: Davies, I.W.; Gerena, L.; Cai, D.; Larsen, R.D.; Verhoeven, T.R.; Reider, P.J. Tetrahedron Lett. 1997, 38, 1145.
188. (a) Ghosh, A.K.; Mathivanan, P.; Cappielo, J. Tetrahedron Lett. 1996, 37, 3815.
189. (b) In a previous work, Ghosh showed that the asymmetric hetero Diels-Alder reaction of Danishefsky diene and glyoxylate esters catalyzed by the chiral Cu(II)-bis(oxazoline) catalyst 137 afforded the hetero Diels-Alder product in 72% enantiomeric excess and 70% isolated yield: Ghosh, A.K.; Mathivanan, P.; Cappielo, J.; Krishnan, P. Tetrahedron:Asymmetry 1996, 7, 2165.
190. (c) For a synthesis of the C3-C14 segment of the antitumor agent laulimalide utilizing a catalytic asymmetric hetero Diels-Alder reaction catalyzed by 137, see: Ghosh, A.K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427.
191. (a) Johannsen, M.; Jorgensen, K.A. J. Org. Chem. 1995, 60, 5757.
192. (b) Johannsen, M.; Jorgensen, K.A. Tetrahedron 1996, 52, 7321.
193. (a) Evans, D.A.; Barnes, D.M. Tetrahedron Lett. 1997, 38, 57.
194. (b) Evans, D.A.; Johnson, J.S. J. Org. Chem. 1997, 62, 786.
195. 1-Tetrahydrocannabinol: Evans, D.A.; Shaughnessy, E.A.; Barnes, D.M. Tetrahedron Lett. 1997, 38, 3193.
196. For interesting papers on the use of competitive complexation NMR studies and AM1 level calculations to describe why do catalytic amounts of Lewis acid generally yield more product than 1.1 equivalents in the intramolecular Diels-Alder reaction with a furan diene, see: (a) Hunt, I.R.; Rogen, C.; Woo, S.; Rauk, A.; Keay, B.A. J. Am. Chem. Soc. 1995, 117, 1049. (b) Hunt, I.R.; Rauk, A.; Keay, B.A. J. Org. Chem. 1996, 61, 751.
197. For interesting papers on the use of competitive complexation NMR studies and AM1 level calculations to describe why do catalytic amounts of Lewis acid generally yield more product than 1.1 equivalents in the intramolecular Diels-Alder reaction with a furan diene, see: (a) Hunt, I.R.; Rogen, C.; Woo, S.; Rauk, A.; Keay, B.A. J. Am. Chem. Soc. 1995, 117, 1049. (b) Hunt, I.R.; Rauk, A.; Keay, B.A. J. Org. Chem. 1996, 61, 751.
198. For a recent review of rare earth triflates in organic synthesis, see: Marshman, R.W. Aldrichimica Acta 1995, 28, 77.
199. Mikami recently reported the use of yttrium (bis-trifylamide) complexes as a new type of asymmetric catalyst for hetero Diels-Alder reactions with Danishefsky diene in the presence of water in up to 66% ee: Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett 1995, 975.
200. Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535.
201. Kobayashi, S.; Araki, M.; Hachiya, I. J. Org. Chem. 1994, 59, 3758.
202. Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623.
203. Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
204. Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325.
205. Markó, I.E.; Evans, G.R. Tetrahedron Lett. 1994, 35, 2771.
206. For more results on this methodology, see: (a) Markó, I.E.; Evans, G.R.; Declerq, J.P.; Feneau-Dupont, J.; Tinant, B. Bull. Soc. Chim. Belg. 1994, 103, 29; (b) Markó, I.E.; Evans, G.R.; Seres, P.; Chellé, I.; Janousek, Z. Pure Appl. Chem. 1996, 68, 113.
207. For more results on this methodology, see: (a) Markó, I.E.; Evans, G.R.; Declerq, J.P.; Feneau-Dupont, J.; Tinant, B. Bull. Soc. Chim. Belg. 1994, 103, 29; (b) Markó, I.E.; Evans, G.R.; Seres, P.; Chellé, I.; Janousek, Z. Pure Appl. Chem. 1996, 68, 113.
208. Markó, I.E.; Evans, G.R.; Declerq, J.P. Tetrahedron 1994, 50, 4557.
209. For the utilization of a C2-symmetric chiral bis(oxazoline)-Fe(III) complex in Diels-Alder additions, see: Corey, E.J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
210. For a very interesting review of C2-symmetric and asymmetric induction, see: Whitesell, J.K. Chem. Rev. 1989, 89, 1581.
211. Corey, E.J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807.
212. For an example of the utilization of Mg(II)-complexes of conformationally constrained bis-(oxazoline) derived chiral catalysts, see Reference 111.
213. (a) In this work, the same reaction in the presence of an Fe(III)-containing catalyst afforded 87% yield of 97 with 99:1 endo:exo selectivity and 86% ee.
214. (b) For one more example of a chiral Fe(III) catalyst, see: Khiar, N.; Fernández, I.; Alardia, F. Tetrahedron Lett. 1993, 34, 123.
215. Fujisawa, T.; Yshiyanagi, T.; Shimizu, M. Tetrahedron Lett. 1995, 36, 5031.
216. (a) Desimoni, G.; Faita, G.; Righetti, P.P. Tetrahedron Lett. 1996, 37, 3027.
217. (b) Desimoni, G.; Faita, G.; Righetti, P.P.; Sardone, N. Tetrahedron 1996, 52, 12019.
218. Ordoñez, M.; la Rosa, V.G.-de; Labartida, V.; Liera, J.M. Tetrahedron:Asymmetry 1996, 7, 2675.
219. Kundig, E.P.; Bourdin, B.; Bernardinelli, G. Angew Chem. Int. Ed. Engl. 1994, 33, 1856.
220. Yamashita, Y.; Katsuki, T. Synlett 1995, 829.
221. Carmona, D.; Cativiela, C.; García-Correas, R.; Lahoz, F.J.; Lamata, M.P.; López, J.A.; López-Ram de Víu, M.P.; Oro, L.A.; San José, E.; Viguri, F. Chem. Commun. 1996, 1247.