Synthesis, Inhaltsverzeichnis SPECIALTOPIC © Georg Thieme Verlag Stuttgart · New York Trans Effect on Cobalt Porphyrin Catalyzed Asymmetric Cyclopropanation Ying Chen, X. Peter Zhang*Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600, USAFax: +1(865)9743454; e-Mail: pzhang@utk.edu; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A significant trans effect of potential coordinating additives was found in asymmetric cyclopropanation catalyzed by Co(II) complexes of D 2 -symmetric chiral porphyrins [Co(1)]. Among different additives, substoichiometric amounts of DMAP resulted in substantial increases in both diastereoselectivity and enantioselectivity. A related solvent effect on the catalytic system was also observed. Key words cyclopropanation - chiral porphyrins - cobalt - trans effect - asymmetric catalysis Volltext Referenzen References 1a Lebel H. Marcoux J.-F. Molinaro C. Charette AB. Chem. Rev. 2003, 103: 977 1b Davies HML. Antoulinakis E. Org. React. 2001, 57: 1 1c Doyle MP. Forbes DC. Chem. Rev. 1998, 98: 911 For selected examples on asymmetric cyclopropanation, see: 2a Evans DA. Woerpel KA. Hinman MM. Faul MF. J. Am. Chem. Soc. 1991, 113: 726 2b Doyle MP. Winchester WR. Hoorn JAA. Lynch V. Simonsen SH. Ghosh R. J. Am. Chem. Soc. 1993, 115: 9968 2c Nishiyama H. Itoh Y. Matsumoto H. Park S.-B. Itoh K. J. Am. Chem. Soc. 1994, 116: 2223 2d Davies HML. Bruzinski PR. Lake DH. Kong N. Fall MJ. J. Am. Chem. Soc. 1996, 118: 6897 2e Lo MM.-C. Fu G. J. Am. Chem. Soc. 1998, 120: 10270 3 The Porphyrin Handbook Kadish KM. Smith KM. Guilard R. Academic Press; San Diego: 2000-2003. Vols. 1-20: 4 For the first report, see: Callot HJ. Piechocki C. Tetrahedron Lett. 1980, 21: 3489 5 For a recent review, see: Simonneaux G. Le Maux PP. In The Porphyrin Handbook Kadish KM. Smith KM. Guilard R. Academic Press; San Diego: 2003. Vol. 11: p.133-159 For selected examples on metalloporphyrin-based asymmetric cyclopropanation, see: 6a Ferrand Y. Le Maux P. Simonneaux G. Org. Lett. 2004, 6: 3211 6b Berkessel A. Kaiser P. Lex J. Chem. Eur. J. 2003, 9: 4746 6c Teng P.-F. Lai T.-S. Kwong H.-L. Che CM. Tetrahedron: Asymmetry 2003, 14: 837 6d Che CM. Huang J.-S. Lee F.-W. Li Y. Lai T.-S. Kwong H.-L. Teng P.-F. Lee W.-S. Lo W.-C. Peng S.-M. Zhou Z.-Y. J. Am. Chem. Soc. 2001, 123: 4119 6e Gross Z. Galili N. Simkhovich L. Tetrahedron Lett. 1999, 40: 1571 6f Maxwell JL. O’Malley S. Brown KC. Kodadek T. Organometallics 1992, 11: 645 For non-porphyrin Co-based cyclopropanation systems, see: 7a Niimi T. Uchida T. Irie R. Katsuki T. Adv. Synth. Catal. 2001, 343: 79 7b Ikeno T. Sato M. Sekino H. Nishizuka A. Yamada T. Bull. Chem. Soc. Jpn. 2001, 74: 2139 7c Nakamura A. Konishi A. Tatsuno Y. Otsuka S. J. Am. Chem. Soc. 1978, 100: 3443 8a Huang L. Chen Y. Gao G.-Y. Zhang XP. J. Org. Chem. 2003, 68: 8179 8b Lee M.-Y. Chen Y. Zhang XP. Organometallics 2003, 22: 4905 8c Chen Y. Zhang XP. J. Org. Chem. 2004, 69: 2431 8d Chen Y. Fields KB. Zhang XP. J. Am. Chem. Soc. 2004, 126: 14718 8e Chen Y. Gao G.-Y. Zhang XP. Tetrahedron Lett. 2005, 46: 4965 9 Penoni A. Wanke R. Tollari S. Gallo E. Musella D. Ragaini F. Demartin F. Cenini S. Eur. J. Inorg. Chem. 2003, 1452