Recent advances in asymmetric [3,3]-sigmatropic rearrangements

Synthesis

Volumn , Issue 7, 2003, Pages 961-1008

  Nubbemeyer, Udo ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Asymmetric Claisen rearrangement; Chiral auxiliary; Chiral catalyst; Chiral metal complex; Cope rearrangement

Indexed keywords

COMPLEXATION; MOLECULAR STRUCTURE; REACTION KINETICS; SYNTHESIS (CHEMICAL);

STEREOGENIC CENTRES;

STEREOCHEMISTRY;

METAL COMPLEX;

ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CLAISEN REARRANGEMENT; COPE REARRANGEMENT; COVALENT BOND; ENANTIOSELECTIVITY; PROCESS CONTROL; REACTION ANALYSIS; REVIEW; SIGMATROPIC REARRANGEMENT; STEREOCHEMISTRY;

EID: 0038695134     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39171     Document Type: Review

References (277)

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117. (b) Ito, H.; Sato, A.; Taguchi, T. Tetrahedron Lett. 1997, 38, 4815.
118. The boron ester formation was crucial for the Claisen rearrangement to proceed. In the absence of an o-OH group the reaction failed. The o-OH group could be replaced by a carboxylic acid function but such conversion resulted a lower yield and a decreased enantioselectivity. Additionally some p-product was isolated.
119. (a) Kazmaier, U.; Mues, H.; Krebs, A. Chem.-Eur. J. 2002, 8, 1850.
120. (b) Mues, H.; Kazmaier, U. Synthesis 2001, 487.
121. (c) Mues, H.; Kazmaier, U. Synlett 2000, 1004.
122. (d) Bakke, M.; Ohta, H.; Kazmaier, U.; Sugai, T. Synthesis 1999, 1671.
123. (e) Krebs, A.; Kazmaier, U. Tetrahedron Lett. 1999, 40, 479.
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125. (g) Kazmaier, U.; Krebs, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2012; Angew. Chem. 1995, 107, 2213.
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127. (h) Kazmaier, U.; Maier, S. J. Chem. Soc., Chem. Commun. 1995, 1991.
128. Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911.
129. However this special variant did obviously not suffer from any von Braun type degradation or from any [2+2]-cycloadditions as reported in previous publications and references cited therein).
130. For potential catalysts see (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336. (b) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
131. For potential catalysts see (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336. (b) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
132. (a) Sugiura, M.; Nakai, T. Tetrahedron Lett. 1996, 37, 7991.
133. (b) Sugiura, M.; Yanagisawa, M.; Nakai, T. Synlett 1995, 447.
134. Reacting non-symmetric enol ethers the palladium-catalyzed version preferentially gave the less-substituted vinyl systems. The rearrangement passed through a boat-like transition state. In contrast the proton-catalyzed reaction gave the higher substituted vinylether and the thermal rearrangement (100 °C) passed through a chair-like transition state. Regio- and stereochemistry could be influenced by a careful choice of the reaction conditions. For the discussion of a two-step reaction mechanism see Overman amidate rearrangements?
135. (a) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 2000, 122, 3785.
136. (b) Trost, B. M.; Toste, D. F. J. Am. Chem. Soc. 1998, 120, 815.
137. (c) For a racemic version see: Gester, S.; Metz, P.; Zierau, O.; Vollmer, G. Tetrahedron 2001, 57, 1015.
138. (d) For a potential racemization during aromatic Claisen rearrangements see: Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41.
139. Generally such intermediate cations could suffer from socalled abnormal 1,3 Claisen rearrangements. A catalytic variant to generate polycyclic terpenoids has been investigated by: (a) Nakamura, S.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 8131. (b) For further 1,3 rearrangements (chirality transfer) see: Shiina, I.; Nagasue, H. Tetrahedron Lett. 2002, 43, 5837. (c) See also: Hashimoto, H.; Jin, T.; Karikomi, M.; Seki, K.; Hagaa, K.; Uyeharaa, T. Tetrahedron Lett. 2002, 43, 3633.
140. Generally such intermediate cations could suffer from socalled abnormal 1,3 Claisen rearrangements. A catalytic variant to generate polycyclic terpenoids has been investigated by: (a) Nakamura, S.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 8131. (b) For further 1,3 rearrangements (chirality transfer) see: Shiina, I.; Nagasue, H. Tetrahedron Lett. 2002, 43, 5837. (c) See also: Hashimoto, H.; Jin, T.; Karikomi, M.; Seki, K.; Hagaa, K.; Uyeharaa, T. Tetrahedron Lett. 2002, 43, 3633.
141. Generally such intermediate cations could suffer from socalled abnormal 1,3 Claisen rearrangements. A catalytic variant to generate polycyclic terpenoids has been investigated by: (a) Nakamura, S.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 8131. (b) For further 1,3 rearrangements (chirality transfer) see: Shiina, I.; Nagasue, H. Tetrahedron Lett. 2002, 43, 5837. (c) See also: Hashimoto, H.; Jin, T.; Karikomi, M.; Seki, K.; Hagaa, K.; Uyeharaa, T. Tetrahedron Lett. 2002, 43, 3633.
142. (a) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371.
143. (b) Drutu, I.; Krygowski, E. S.; Wood, J. L. J. Org. Chem. 2001, 66, 7025.
144. (c) For a direct allylation of diazoketones as a surrogate for catalyzed enantioselective Claisen rearrangements see: Davies, H. M. L.; Ren, P.; Jin, Q. Org. Lett. 2001, 3, 3587.
145. The rhodium catalyst did not influence the Claisen rearrangement step.
146. (a) Miller, S. P.; Morken, J. P. Org. Lett. 2002, 4, 2743.
147. (b) For further tandem processes see: Diels-Alder/Claisen: Soldermann, N.; Velker, J.; Vallat, O.; Stoeckli-Evans, H.; Neier, R. Helv. Chim. Acta 2000, 83, 2266.
148. (c)Frank, S. A.; Works, A. B.; Roush, W. R. Can. J. Chem. 2000, 78, 757.
149. (a) Wipf, P.; Ribe, S. Org. Lett. 2001, 3, 1503.
150. (b) The Claisen rearrangement is an ideal precursor for olefin converting consecutive processes such as metathesis dihydroxylations etc.
151. (a) Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem. Int. Ed. 2001, 40, 4700; Angew. Chem. 2001, 113, 4835.
152. (a) Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem. Int. Ed. 2001, 40, 4700; Angew. Chem. 2001, 113, 4835.
153. (b) For catalyzed racemic rearrangements see: Hiersemann, M.; Abraham, L. Org. Lett. 2001, 3, 49.
154. (c) Hiersemann, M. Synthesis 2000, 1279.
155. (d) Kaden, S.; Hiersemann, M. Synlett 2002, 1999.
156. (a) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449.
157. (b) Kollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837.
158. (c) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213.
159. (d) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933.
160. (e) For the thermal and palladium-catalyzed racemic rearrangement see: Overman, L. E.; Zipp, G. G. J. Am. Chem. Soc. 1997, 62, 2288.
161. Kang, J.; Yew, K. H.; Kim, T. H.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509.
162. (a) Jiang, Y.; Lougmire, J. M.; Zhang, X. Tetrahedron Lett. 1999, 40, 1449.
163. (b) Leung, P.-H.; Ng, K.-H.; Li, Y.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1999, 2435.
164. (c) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
165. Gais, H,-J.; Böhme, A. J. Org. Chem. 2002, 67, 1153.
166. For an aza-Cope-Mannich tandem process see: (a) Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776. (b) For oxy-Cope-aldol tandem process see ref.
167. For an aza-Cope-Mannich tandem process see: (a) Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776. (b) For oxy-Cope-aldol tandem process see ref.
168. Low stereoselectivities were observed in several anionic oxy-Cope rearrangements: Lee, Y.; Lee, Y. R.; Moon, O.; Kwon, O.; Shim, M. S.; Yun, J. S. J. Org. Chem. 1994, 59, 1444.
169. For an example where a chiral chromium arene complex did not affect the stereochemical outcome of a Cope rearrangement see: (a) Mandal, S. K.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 2002, 669. (b) For an aza-Cope rearrangement via chromium carbene complexes see: Barluenga, J.; Tomas, M.; Ballesteros, A.; Santamaria, J.; Suarez-Sobrino, A. J. Org. Chem. 1997, 62, 9229.
170. For an example where a chiral chromium arene complex did not affect the stereochemical outcome of a Cope rearrangement see: (a) Mandal, S. K.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 2002, 669. (b) For an aza-Cope rearrangement via chromium carbene complexes see: Barluenga, J.; Tomas, M.; Ballesteros, A.; Santamaria, J.; Suarez-Sobrino, A. J. Org. Chem. 1997, 62, 9229.
171. (a) Kuehne, M. E.; Xu, F. J. Org. Chem. 1997, 62, 7950.
172. (b) Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9427.
173. (c) Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9434.
174. Deloisy, S.; Kunz, H. Tetrahedron Lett. 1998, 39, 791.
175. (a) Cardoso, A. S.; Lobo, A. M.; Prabhakar, S. Tetrahedron Lett. 2000, 41, 3611.
176. (b) Depew, K. M.; Danishefsky, S. J.; Rosen, N.; Sepp-Lorenzino, L. J. Am. Chem. Soc. 1996, 118, 12463.
177. The 3,5-rearrangement can be described as an iminium salt olefin addition and a subsequent fragmentation (cation stabilization). No new stereogenic center was constructed.
178. Román, E.; Baños, M.; Higes, F. J.; Serrano, J. A. Tetrahedron: Asymmetry 1998, 9, 449.
179. Agami, C.; Couty, F.; Puchot-Kadouri, C. Synlett 1998, 449.
180. (a) Nokami, J.; Ohga, M.; Nakamoto, H.; Matsubara, T.; Hussain, I.; Kataoka, K. J. Am. Chem. Soc. 2002, 123, 9168.
181. (b) For preliminary publications see: Nokami, J.; Anthony, L.; Sumida, S. Chem.-Eur. J. 2000, 6, 2909; concept.
182. (c) See also: Sumida, S.; Ohga, M.; Mitani, J.; Nokami, J. J. Am. Chem. Soc. 2000, 122, 1310.
183. (d) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609.
184. (e) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426.
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186. The reversibility of the Cope rearrangement might cause some racemization - the avoiding of such a process was recommended. Alternatively a Prins cyclization could be discussed as the basic reaction mechanism. Cope rearrangements were found to be much faster than the Prins reaction. For the role of oxonia Cope rearrangements in Prins cyclizations see: (a) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815. (b) Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919.
187. The reversibility of the Cope rearrangement might cause some racemization - the avoiding of such a process was recommended. Alternatively a Prins cyclization could be discussed as the basic reaction mechanism. Cope rearrangements were found to be much faster than the Prins reaction. For the role of oxonia Cope rearrangements in Prins cyclizations see: (a) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815. (b) Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919.
188. (a) Allin, S. M.; Baird, R. D.; Lins, R. J. Tetrahedron Lett. 2002, 43, 4195.
189. (b) Allin, S. M.; Button, M. A. C.; Baird, R. D. Synlett 1998, 1117.
190. (c) Allin, S. M.; Button, M. A. C. Tetrahedron Lett. 1998, 39, 3345-3348.
191. (d) For preliminary publications see: Allin, S. M.; Button, M. A. C.; Shuttleworth, S. J. Synlett 1997, 725.
192. n-BuLi was found to be the base of choice to induce the anionic amino Cope rearrangements. Experiments using alternative strong bases such as LDA and KHMDS failed.
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