Dr. P. Wipf Page 1 of 5 10/7/2009. Cl Ru. Kingsbury, J. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
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1 Dr. P. Wipf Page 1 of 5 10/7/2009 Alkene Metathesis Grubbs II published The Catalysts Me Mo F 3C CF3 Me F 3C CF3 C(Me) 2 chrock, R. R.; Murdzek, J..; Bazan, G. C.; Robbins, J.; DiMare, M.; 'Reagan, M. J. Am. Chem. oc. 1990, 112, 3875 chrock I Cy 3P 3 2( 3) 2=C chwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R.. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039 Grubbs I Kingsbury, J..; arrity, J. P. A.; oveyda, A.. J. Am. Chem. oc. 1999, 121, ( 2I)( 3) 2=C choll, M.; Ding,.; Lee, C. W.; Grubbs, R.. rg. Lett. 1999, 1, 953 Grubbs II ( 2I)(3--py) 2 2=C Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R.. Angew. Chem. Int. Ed. 2002, 41, 4035 Grubbs III Green Grubbs english/products/ Zhan-1B Me 2 oveyda, A..; Zhugralin, A. R., "The remarkable metal-catalysed olefin metathesis reaction." ature 2007, 450,
2 Dr. P. Wipf Page 2 of 5 10/7/2009 Ring-osing Metathesis (RCM) and Ring-pening Metathesis (RMP) The obel Prize in Chemistry 2005 Yves Chauvin Institut Français du Pétrole, eil-malmaison, France, Robert. Grubbs California Institute of Technology (Caltech), Pasadena, CA, UA and Richard R. chrock Massachusetts Institute of Technology (MIT), Cambridge, MA, UA "for the development of the metathesis method in organic synthesis". Introduction RCM Cross-Metathesis RMP Important types of metathesis reactions: RCM = ring-closing metathesis RM = ring-opening metathesis RMP = ring-opening metathesis polymerization RCM -C 2 4 RM +C 2 4 RMP ADMET = acyclic diene metathesis polymerization CM = cross-metathesis ADMET -nc 2 4 M n CM -C 2 4 R2
3 Dr. P. Wipf Page 3 of 5 10/7/2009 thenium-based lefin Metathesis The synthesis of ruthenium vinylcarbene complexes allowed the development of well-defined, late transition metal, low oxidation state complexes that catalyze olefin metathesis. thenium carbene complexes are significantly easier to make and handle than the chrock molybdenum complex. In addition to the metathesis of strained cyclic and exocyclic olefins, the remarkable functional group tolerance (alcohols, aldehydes, carboxylic acids) and stability toward air, water, and acid has made this class of compounds particularly attractive for practical applications (Grubbs, R..; Miller,. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446). thenium-based lefin Metathesis: Applications Manzamine A Mo CF 3 A 3 3 B C 2Me C 2 Et C 2BDP B, 1equiv. rt, 5 days 30% Pandit, TL 1994, 35, 3191 C 2BDP (Z only) C 2Me A, benzene 50 C, 63% C 2Me Martin, TL 1994, 35,691 Large-scale preparation of pharmaceutical candidates: epatitis C protease inhibitor BIL 2061 developed by Boehringer-Ingelheim C 2 Me Me P toluene, 80 C >400 kg scale 83%, >99% cis C 2 Me BIL 2061 C 2
4 Dr. P. Wipf Page 4 of 5 10/7/2009 Liverton,. J.; olloway, M. K.; Mccauley, J. A.; dd, M. T.; Butcher, J. W.; Carroll,..; Dimuzio, J.; Fandozzi, C.; Gilbert, K. F.; Mao,.-.; Mcintyre, C. J.; guyen, K. T.; Romano, J. J.; tahlhut, M.; Wan, B.-L.; lsen, D. B.; Vacca, J. P., "Molecular modeling based approach to potent P2-P4 macrocyclic inhibitors of hepatitis C 3/4A protease." J. Am. Chem. oc. 2008, 130, C 2 Boc e) Zhan catalyst, DCE, ~10 mm, 83% f) 2, 10% Pd/C, EtAc, quant. a) KtBu, DMF b), Et, 65% (2 steps) Me 2 double bond single bond C 2 Et C 2 Et g) Li, TF, Me, 2 h) ATU, DIPEA, DMAP, DMF, 93% 2 C 2 c) ATU, DIPEA, DMF, 74% d) Bu 3 nc=c 2, Pd(P 3 ) 4, toluene, 100 o C, 87% R MK-7009 R = R = vinyl C 2 Et Wipf, P.; pencer,. R. "Asymmetric total syntheses of tuberostemonine, didehydrotuberostemonine, and 13-epituberostemonine." J. Am. Chem. oc. 2005, 127, C 2 Me C 2 Me Cbz Tuberostemonine Tyrosine 2 C 2 Azepine Annulation via RCM,-Dimethylacetamide dimethyl acetal xylenes; 79% 2 (=C)( 3 ) 2 C 2 2 ; 72% e, C 2 2 Bu 3 nc 2 C=C 2-78 C; 20% e AIB, toluene, 100 C; 42%
5 Dr. P. Wipf Page 5 of 5 10/7/2009 C 2 Me 3 C 2 2 ; 92% C 2 Me 1., TEA 2. ( 3 P) 3 Rh, 2 3. DBU, TF; 76% C 2 Me 1. ab 4, Ce 3 ; 75% 2. TB-, Im.; 79% 3. MeMe, Me 2 Al; 94% TB Me, LiDBB TF, -78 C; 81% TB 1. L-electride 2. Ts, Me 75%,-Dimethylacetamide dimethyl acetal xylenes; 79% Me 2 1. e, MeC/ 2, 0 C; 67% 2. AIB, allyltriphenyltin, 95 C; 70% 3. LDA MPA, TF; MeI 76% 3 toluene; 85% Tr C 2 2 ; 2 C=C 2 ; then Pd/C, 2, Me; 80% Tuberostemonine! 27 steps/1.1% yield from Cbz-tyrosine Why Carbene Ligands? The nucleophilic carbenes are phosphine-mimics and yet they are much more. They reside at the upper end of the Tolman electronic and steric parameter scales. From solution calorimetric studies, it became clear that nucleophilic carbenes (most of them) are better donors than the best donor phosphines.
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