Synthesis, Table of Contents SPECIALTOPIC© Georg Thieme Verlag Stuttgart · New York Trans Effect on Cobalt Porphyrin Catalyzed Asymmetric CyclopropanationYing Chen, X. Peter Zhang*Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600, USAFax: +1(865)9743454; e-Mail: pzhang@utk.edu; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References <A NAME="RC00306SS-1A">1a</A> Lebel H. Marcoux J.-F. Molinaro C. Charette AB. Chem. Rev. 2003, 103: 977 <A NAME="RC00306SS-1B">1b</A> Davies HML. Antoulinakis E. Org. React. 2001, 57: 1 <A NAME="RC00306SS-1C">1c</A> Doyle MP. Forbes DC. Chem. Rev. 1998, 98: 911 For selected examples on asymmetric cyclopropanation, see: <A NAME="RC00306SS-2A">2a</A> Evans DA. Woerpel KA. Hinman MM. Faul MF. J. Am. Chem. Soc. 1991, 113: 726 <A NAME="RC00306SS-2B">2b</A> Doyle MP. Winchester WR. Hoorn JAA. Lynch V. Simonsen SH. Ghosh R. J. Am. Chem. Soc. 1993, 115: 9968 <A NAME="RC00306SS-2C">2c</A> Nishiyama H. Itoh Y. Matsumoto H. Park S.-B. Itoh K. J. Am. Chem. Soc. 1994, 116: 2223 <A NAME="RC00306SS-2D">2d</A> Davies HML. Bruzinski PR. Lake DH. Kong N. Fall MJ. J. Am. Chem. Soc. 1996, 118: 6897 <A NAME="RC00306SS-2E">2e</A> Lo MM.-C. Fu G. J. Am. Chem. Soc. 1998, 120: 10270 <A NAME="RC00306SS-3">3</A> The Porphyrin Handbook Kadish KM. Smith KM. Guilard R. Academic Press; San Diego: 2000-2003. Vols. 1-20: <A NAME="RC00306SS-4">4</A> For the first report, see: Callot HJ. Piechocki C. Tetrahedron Lett. 1980, 21: 3489 <A NAME="RC00306SS-5">5</A> 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: <A NAME="RC00306SS-6A">6a</A> Ferrand Y. Le Maux P. Simonneaux G. Org. Lett. 2004, 6: 3211 <A NAME="RC00306SS-6B">6b</A> Berkessel A. Kaiser P. Lex J. Chem. Eur. J. 2003, 9: 4746 <A NAME="RC00306SS-6C">6c</A> Teng P.-F. Lai T.-S. Kwong H.-L. Che CM. Tetrahedron: Asymmetry 2003, 14: 837 <A NAME="RC00306SS-6D">6d</A> 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 <A NAME="RC00306SS-6E">6e</A> Gross Z. Galili N. Simkhovich L. Tetrahedron Lett. 1999, 40: 1571 <A NAME="RC00306SS-6F">6f</A> Maxwell JL. O’Malley S. Brown KC. Kodadek T. Organometallics 1992, 11: 645 For non-porphyrin Co-based cyclopropanation systems, see: <A NAME="RC00306SS-7A">7a</A> Niimi T. Uchida T. Irie R. Katsuki T. Adv. Synth. Catal. 2001, 343: 79 <A NAME="RC00306SS-7B">7b</A> Ikeno T. Sato M. Sekino H. Nishizuka A. Yamada T. Bull. Chem. Soc. Jpn. 2001, 74: 2139 <A NAME="RC00306SS-7C">7c</A> Nakamura A. Konishi A. Tatsuno Y. Otsuka S. J. Am. Chem. Soc. 1978, 100: 3443 <A NAME="RC00306SS-8A">8a</A> Huang L. Chen Y. Gao G.-Y. Zhang XP. J. Org. Chem. 2003, 68: 8179 <A NAME="RC00306SS-8B">8b</A> Lee M.-Y. Chen Y. Zhang XP. Organometallics 2003, 22: 4905 <A NAME="RC00306SS-8C">8c</A> Chen Y. Zhang XP. J. Org. Chem. 2004, 69: 2431 <A NAME="RC00306SS-8D">8d</A> Chen Y. Fields KB. Zhang XP. J. Am. Chem. Soc. 2004, 126: 14718 <A NAME="RC00306SS-8E">8e</A> Chen Y. Gao G.-Y. Zhang XP. Tetrahedron Lett. 2005, 46: 4965 <A NAME="RC00306SS-9">9</A> Penoni A. Wanke R. Tollari S. Gallo E. Musella D. Ragaini F. Demartin F. Cenini S. Eur. J. Inorg. Chem. 2003, 1452