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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 557-564

http://dx.doi.org/10.1351/pac200476030557

Stereochemistry of epoxide carbonylation using bimetallic Lewis acid/metal carbonyl complexes

Y. D. Y. L. Getzler, Viswanath Mahadevan, E. B. Lobkovsky and G. W. Coates

Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853-1301, USA

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  • Mulzer Michael, Ellis W. Chadwick, Lobkovsky Emil B., Coates Geoffrey W.: Enantioenriched β-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides. Chem. Sci. 2014, 5, 1928. <http://dx.doi.org/10.1039/c4sc00075g>
  • Miranda Maria O., DePorre Yvonne, Vazquez-Lima Hugo, Johnson Michelle A., Marell Daniel J., Cramer Christopher J., Tolman William B.: Understanding the Mechanism of Polymerization of ε-Caprolactone Catalyzed by Aluminum Salen Complexes. Inorg. Chem. 2013, 52, 13692. <http://dx.doi.org/10.1021/ic402255m>
  • Mulzer Michael, Whiting Bryan T., Coates Geoffrey W.: Regioselective Carbonylation of trans-Disubstituted Epoxides to β-Lactones: A Viable Entry into syn-Aldol-Type Products. J. Am. Chem. Soc. 2013, 135, 10930. <http://dx.doi.org/10.1021/ja405151n>
  • FAN Qijia, LIU Jianhua, CHEN Jing, XIA Chungu: Recent Progress in Carbonylation of Epoxides. CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION) 2013, 33, 1435. <http://dx.doi.org/10.3724/SP.J.1088.2012.20515>
  • Ganji Prasad, Ibrahim Hasim: The first asymmetric ring-expansion carbonylation of meso-epoxides. Chem. Commun. 2012, 48, 10138. <http://dx.doi.org/10.1039/c2cc35596e>
  • Wölfle Heimo, Kopacka Holger, Wurst Klaus, Preishuber-Pflügl Peter, Bildstein Benno: On the way to biodegradable poly(hydroxy butyrate) from propylene oxide and carbon monoxide via β-butyrolactone: Multisite catalysis with newly designed chiral indole-imino chromium(III) complexes. J Organomet Chem 2009, 694, 2493. <http://dx.doi.org/10.1016/j.jorganchem.2009.04.013>
  • Permana Yessi, Nakano Koji, Yamashita Makoto, Watanabe Daisuke, Nozaki Kyoko: Carbonylative Polymerization of Oxetanes Initiated by Acetyl Cobalt Complexes. Chem Asian J 2008, 3, 710. <http://dx.doi.org/10.1002/asia.200700339>
  • Xu Liwen, Chen Jing, Xia Chungu, Liu Jianhua, Wu Hugjiltu: A novel and highly effective catalytic system for alkoxycarbonylation of (S)-propylene oxide. Journal of Molecular Catalysis A 2007, 269, 97. <http://dx.doi.org/10.1016/j.molcata.2006.12.045>
  • Church Tamara L., Getzler Yutan D. Y. L., Byrne Christopher M., Coates Geoffrey W.: Carbonylation of heterocycles by homogeneous catalysts. Chem Commun 2007, 657. <http://dx.doi.org/10.1039/b613476a>
  • Liu Jianhua, Chen Jing, Xia Chungu: Methoxycarbonylation of propylene oxide: A new way to β-hydroxybutyrate. Journal of Molecular Catalysis A 2006, 250, 232. <http://dx.doi.org/10.1016/j.molcata.2006.01.047>
  • Kramer John W., Lobkovsky Emil B., Coates Geoffrey W.: Practical β-Lactone Synthesis:  Epoxide Carbonylation at 1 atm. Org Lett 2006, 8, 3709. <http://dx.doi.org/10.1021/ol061292x>
  • Xu Hongyu, Gladding Jeffery A., Jia Li: Stereochemistry of cobalt-catalyzed carbonylation of 2-oxazolines. Inorganica Chimica Acta 2004, 357, 4024. <http://dx.doi.org/10.1016/j.ica.2004.07.040>