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Ring-Closing Metathesis of Allylic O,O- and N,O-Acetals

2002; Wiley; Volume: 344; Issue: 6-7 Linguagem: Inglês

10.1002/1615-4169(200208)344

1615-4169

Sape S. Kinderman, Robin Doodeman, Jetze W. van Beijma, Jaap C. Russcher, Kim C. M. F. Tjen, T.M. Kooistra, Homayun Mohaselzadeh, Jan H. van Maarseveen, Henk Hiemstra, Hans E. Schoemaker, Floris P. J. T. Rutjes,

Synthetic Organic Chemistry Methods

Advanced Synthesis & CatalysisVolume 344, Issue 6-7 p. 736-748 Full Paper Ring-Closing Metathesis of Allylic O,O- and N,O-Acetals Sape S. Kinderman, Sape S. Kinderman Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorRobin Doodeman, Robin Doodeman Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorJetze W. van Beijma, Jetze W. van Beijma Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorJaap C. Russcher, Jaap C. Russcher NSR Center, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The NetherlandsSearch for more papers by this authorKim C. M. F. Tjen, Kim C. M. F. Tjen Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorT. Martijn Kooistra, T. Martijn Kooistra Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorHomayun Mohaselzadeh, Homayun Mohaselzadeh Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorJan H. van Maarseveen, Jan H. van Maarseveen Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorHenk Hiemstra, Henk Hiemstra Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorHans E. Schoemaker, Hans E. Schoemaker Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorFloris P. J. T. Rutjes, Floris P. J. T. Rutjes Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this author Sape S. Kinderman, Sape S. Kinderman Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorRobin Doodeman, Robin Doodeman Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorJetze W. van Beijma, Jetze W. van Beijma Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorJaap C. Russcher, Jaap C. Russcher NSR Center, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The NetherlandsSearch for more papers by this authorKim C. M. F. Tjen, Kim C. M. F. Tjen Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorT. Martijn Kooistra, T. Martijn Kooistra Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorHomayun Mohaselzadeh, Homayun Mohaselzadeh Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorJan H. van Maarseveen, Jan H. van Maarseveen Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorHenk Hiemstra, Henk Hiemstra Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorHans E. Schoemaker, Hans E. Schoemaker Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this authorFloris P. J. T. Rutjes, Floris P. J. T. Rutjes Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The NetherlandsSearch for more papers by this author First published: 20 August 2002 https://doi.org/10.1002/1615-4169(200208)344:6/7 3.0.CO;2-8Citations: 62AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract A variety of allylic O,O- and N,O-acetals were synthesized using a mild palladium-catalyzed coupling of an alcohol or sulfonamide with an alkyl or aryl 1,2-propadienyl ether. The resulting linear acetals were used for the synthesis of unsaturated rings via ring-closing metathesis, in which the acetal carbon–a precursor for oxycarbenium or N-sulfonyliminium ions, respectively–served as a reactive center for further introduction of functional groups. The products–unsaturated oxygen and nitrogen heterocyclic scaffolds–offer multiple opportunities for derivatization as illustrated with the synthesis of substituted dihydropyrans, chromenes, enantiopure tetrahydropyridines and an enantiomerically pure quinolizidine amino acid. References 1 For review articles, see: 1a A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012; 1b T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; 1c R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413. 1d A. Fürstner, Top. Organomet. Chem. 1998, 1, 37. 2 For several investigations into new RCM catalysts, see: 2a J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674; 2b M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247; 2c M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953; 2d S. S. Zhu, D. R. Cefalo, D. S. La, J. Y. Jamieson, W. M. Davis, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 1999, 121, 8251; 2e G. S. Wheaterhead, J. G. Ford, E. J. Alexanian, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 1828; 2f A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236. 3a F. P. J. T. Rutjes, T. M. Kooistra, H. Hiemstra, H. E. Schoemaker, Synlett 1998, 192; 3b M. T. Crimmins, B. W. King, J. Am. Chem. Soc. 1998, 120, 9084; 3c H. Ovaa, M. A. Leeuwenburgh, H. S. Overkleeft, van der Marel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 3025; 3d P. A. V. van Hooft, M. A. Leeuwenburgh, H. S. Overkleeft, van der Marel, C. A. A. van Boeckel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 6061; 3e M. Scholl, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 1425; 3f M. J. Bassindale, P. Hamley, A. Leitner, J. P. A. Harrity, Tetrahedron Lett. 1999, 40, 3247; 3g K. C. M. F. Tjen, S. S. Kinderman, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Chem. Commun. 2000, 699; 3h R. Doodeman, F. P. J. T. Rutjes, H. Hiemstra, Tetrahedron Lett. 2000, 41, 5979; 3i J. Mulzer, M. Hanbauer, Tetrahedron Lett. 2000, 41, 33. For a silicon tethered example, see: T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429 and references cited therein. 4 Some recent selected examples on dihydropyrans: 4a B. Schmidt, H. Wildemann, Eur. J. Org. Chem. 2000, 3145; 4b A. K. Ghosh, H. Lei, J. Org. Chem. 2000, 65, 4779; 4c D. P. Steinhuebel, J. J. Fleming, Du Bois, Org. Lett. 2002, 4, 293; 4d T. B. Durham, M. J. Miller, Org. Lett. 2002, 4, 135. For examples on tetrahydropyridines and azepines, see: 4e J. Åhman, P. Somfai, Tetrahedron Lett. 1995, 36, 303; 4f S. N. Osipov, N. M. Kobelíkova, G. T. Shchetnikov, A. F. Kolomiets, C. Bruneau, P. H. Dixneuf, Synlett 2001, 621; 4g W. H. Pearson, A. Aponick, Org. Lett. 2001, 3, 1327. For examples on chromenes, see: 4h B. M. Trost, F. D. J. Toste, J. Am. Chem. Soc. 1998, 120, 9074. 4i K. S. Atwal, G. J. Grover, F. N. Ferrara, S. Z. Ahmd, P. G. Sleph, S. Dzwonczyk, D. E. Normandin, J. Med. Chem. 1995, 38, 1966. 5 For examples, see: 5a S. A. Angle, J. G. Breitenbucher, Tetrahedron Lett. 1993, 34, 3985; 5b T. Hamada, T. Zenkoh, H. Sato, O. Yonemitsu, Tetrahedron Lett. 1991, 32, 1649; 5c T. Bauer, C. Chapuis, A. Jezewski, J. Kozak, J. Jurczak, Tetrahedron: Asymmetry 1996, 7, 1391; 5d T. Bauer, A. Jezewski, J. Jurczak, Tetrahedron: Asymmetry 1996, 7, 1405; 5e M. Terada, K. Mikami, T. Nakai, Tetrahedron Lett. 1991, 32, 935. The dihydropyran as a useful building block in the total synthesis of fostriecin (CI-920): 5f D. L. Boger, S. Ichikawa, W. Zhong, J. Am. Chem. Soc. 2001, 123, 4161. 6a G. C. Fu, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1993, 115, 9856; 6b A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, M. R. Giles, E. L. Marshall, P. A. Procopiou, A. J. P. White, D. J. Williams, J. Org. Chem. 1998, 63, 7893. 7 For an entry into applications of the strongly related N-acyliminium ion intermediates, see: W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817. 8 A detailed account on mechanistic aspects of Pd-mediated coupling reactions of alkoxyallenes with amines and alcohols will be published in the near future. 9 For a discussion on metathesis cyclizations of vinylglycine-derived substrates, see: J.-M. Campagne, L. Ghosez, Tetrahedron Lett. 1998, 39, 6175. 10a L. B. Wolf, T. Sonke, K. C. M. F. Tjen, B. Kaptein, Q. B. Broxterman, H. E. Schoemaker, F. P. J. T. Rutjes, Adv. Synth. Catal. 2001, 343, 662; 10b T. Sonke, B. Kaptein, W. H. J. Boesten, Q. B. Broxterman, J. Kamphuis, F. Formaggio, C. Toniolo, F. P. J. T. Rutjes, H. E. Schoemaker, in Stereoselective Biocatalysis, ( ), Marcel Dekker, New York, 2000, pp. 23–59. 11 For examples of formation of sulfonyl-protected N,O-acetals, see e. g.: 11a T. Shono, Y. Matsumura, S. Katoh, K. Takeuchi, K. Sasaki, T. Kamada, R. Shimizu, J. Am. Chem. Soc. 1990, 112, 2368; 11b R. Consonni, P. D. Croce, R. Ferraccioli, J. Heterocycl. Chem. 1990, 27, 427. 12 For recent examples of Pd-catalyzed allylic O,O-acetal formation and subsequent functionalization in natural product synthesis, see e. g.: 12a C. Held, R. Fröhlich, P. Metz, Angew. Chem. Int. Ed. 2001, 40, 1058; 12b G. T. Nadolski, B. S. Davidson, Tetrahedron Lett. 2001, 42, 797. 13 For alternative metathesis approaches towards substituted chromenes, see e. g.: 13a S. Chang, R. H. Grubbs, J. Org. Chem. 1998, 63, 864; 13b J. P. A. Harrity, D. S. La, D. R. Cefalo, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1998, 120, 2343; 13c P. Wipf, W. S. Weiner, J. Org. Chem. 1999, 64, 5321. 14 L. Brandsma, H. D. Verkruijsse, Synthesis of acetylenes, allenes and cumulenes, a laboratory manual, in Studies in Organic Chemistry, Vol. 8, Elsevier, Amsterdam, 1981. 15 S. D. Bull, S. G. Davies, S. W. Epstein, M. A. Leech, J. V. A. Ouzman, J. Chem. Soc. Perkin Trans. 1 1998, 2321. 16 Isolation: F. E. King, T. J. King and A. J. Warwick, J. Chem. Soc. 1950, 3590. For other recent enantiopure syntheses of baikiain, see: 16a X. Ginesta, M. A. Pericàs, A. Riera, Tetrahedron Lett. 2002, 43, 779; 16b G. Guillena, C. Nájera, J. Org. Chem. 2000, 65, 7310; 16c A. Mazon, C. Nájera, Tetrahedron: Asymmetry 1997, 11, 1855. 17 Such a high diastereoselectivity has been observed in comparable systems without the unsaturation: C. Yang, Y. Xu, L. Liao, W. Zhou, Tetrahedron Lett. 1998, 39, 9228 and references cited therein. 18 For a highlight on methyl propadienyl ether: R. Pulz, Synlett 2000, 1697. 19 For a review on alkoxy-1,2-propadienes, see: R. Zimmer, Synthesis 1993, 167. Citing Literature Volume344, Issue6-7August 2002Pages 736-748 ReferencesRelatedInformation