Cyclopropanation of Various Substrates via Simmons-Smith and Michael-Initiated Ring Closure (MIRC) Reactions
Abstract

References
Donaldson, W.A., 2001. Synthesis of Cyclopropane Containing Natural Products. Tetrahedron, 57, 8589 [2] Saläun, 2000. Cyclopropane Derivatives and Their Diverse Biological Activities. Top. Curr. Chem., 207, 1 [3] Wallock, N.J., 2004. Preparation of Cyclopropanes via Organoiron Methodology, Dissertation, Marquette University [4] Hoffmann, N., 2008. Chemical Reviews. Chem. Rev., 108, 1052 [5] Asai, A. et al., 2000. Belactosin A, A Novel Antitumor Antibiotic Acting on Cyclin/CDK Mediated Cell Cycle Regulation, Produced by Streptomyces sp. J. Antibiotics, 53, 81 [6] Friesen, R.W. et al., 2003. Optimization of A Tertiary Alcohol Series of Phosphodiesterase-4 (PDE4) Inhibitors: Structure-Activity Relationship Related to PDE4 Inhibition and Human Ether-a-go-go Related Gene Potassium Channel Binding Affinity. J. Med. Chem., 46, 2413 [7] Deng, Y. et al., 2009. Bioactive 5,6-Dihydro-α-pyrone Derivatives from Hyptis brevipes. J. Nat. Prod., 72, 1165–1169 [8] Suárez-Ortiz, G.A. et al., 2013. Absolute Configuration and Conformational Analysis of Brevipolides, Bioactive 5,6-Dihydro-α-pyrones from Hyptis brevipes. J. Nat. Prod., 76, 72−78 [9] Lin, J.-W. et al., 2014. Asymmetric Synthesis of (−)-Brevipolide H through Cyclopropanation of the α,β-Unsaturated Ketone. Org. Lett., 16 (20), pp 5328-5331 [10] Narayanam, J.M. and Stephenson, C.R., 2011. Visible Light Photoredox Catalysis: Applications in Organic Synthesis. Chem. Soc. Rev., 40, 102 [11] Kavarnos, G.J. and Turro, N.J., 1986. Photosensitization by Reversible Electron Transfer: Theories, Experimental Evidence, and Examples. Chem. Rev., 86, 401 [12] Cornwall, R.G. et al., 2012. A Novel Class of Tunable Cyclopropanation Reagents (RXZnCH) and Their Synthetic Applications. Org. Biomol. Chem., 10, 5498 [13] Corey, E.J. and Chaykovsky, M., 1965. Dimethyloxosulfonium Methylide ((CH3)2SOCH2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic Synthesis. J. Am. Chem. Soc., 1353−1364 [14] Simmons, H.E. and Smith, R.D., 1958. A New Synthesis of Cyclopropanes from Olefins. J. Am. Chem. Soc., 80, 5323 [15] Simmons, H.E. and Smith, R.D., 1959. A New Synthesis of Cyclopropanes1. J. Am. Chem. Soc., 81, 4256 [16] Charette, A.B. and Molinaro, C., 2003. Stereoselective Cyclopropanation Reactions. Chem. Rev., 103, 977−1050 [17] Furukawa, J. and Kawabata, N., 1966. A Novel Route to Cyclopropane from Olefins. Tetrahedron Lett., 7, 3353 [18] Ma, D. and Ma, Z., 1997. Facile Synthesis of (2S,l’S,2’S)-2-(Carboxycyclopropyl) glycine, an Isotype-Selective Agonist of Metabotropic Glutamate Receptors. Tetrahedron Lett., 38, 7599 [19] Lu, K.-J. and Hou, D.-R., 2009. Synthesis and Stereochemical Assignment of (+)-Cladospolide D. Tetrahedron, 65, 225–231 [20] Voigtritter, K. and Lipsshutz, B.H., 2011. Rate Enhanced Olefin Cross-Metathesis Reactions: the Copper Iodide Effect. J. Org. Chem., 76, 4697-4702 [21] Burke, S.D. and Sametz, G.M., 1999. Total Synthesis of 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and 2-Deoxy-β-KDO. Org. Lett., 1, 71-74 [22] Caroline, C.R. and Benazza, M., 1997. Efficient Synthesis of α,ω-Dibromodideoxyalditols as Precursors for α,ω -Dithioalkylalditols. Carbohydrate Research., 303, 359-365 [23] Liu, C.-W. and Hou, D.-R., 2013. Total Synthesis of 14,21-Diepi-squamocin-K. Tetrahedron, 69, 2971-2976 [24] Takashi, H. et al., 1995. A Catalytic Enantioselective Reaction Using a C2-Symmetric Disulfonamide as a Chiral Ligand: Simmons-Smith Cyclopropanation of Allylic Alcohols by the EtzZn-CH2I2-Disulfonamide System. Tetrahedron, Vol. 51, No. 44, 12013-12026 [25] Kurniawan, Y.D. and Hou, D.-R., 2014. Practical Preparation of (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate. J. Pure App. Chem. Res., 3 (1), 13‐18
Refbacks
- There are currently no refbacks.