Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Diastereoselective Synthesis of trans β-Lactams on Soluble Polymer Support Shan-Zhong Jian, Qing Yuan, Yan-Guang Wang*Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of ChinaFax: +86(571)87951512; e-Mail: orgwyg@zju.edu.cn; Recommend Article Abstract Buy Article All articles of this category Abstract Liquid-phase synthesis of trans b-lactams was accomplished through both PEG-supported imine and PEG-bound auxiliary methodologies. The trans diastereoselectivity is explained by a chair-like transition state involving the imine and the Z-enolate. Key words lactam - PEG - Reformatsky reaction - resin-capture-release - Z-enolate Full Text References References 1a Lam KSM. Lebl M. Krchnak V. Chem. Rev. 1997, 97: 411 1b Krchnak V. Holladay MW. Chem. Rev. 2002, 102: 61 1c Blaney P. Grigg R. Sridharan V. Chem. Rev. 2002, 102: 2607 1d Balkenhohl F. von dem Bussche-Hunnefeld CVD. Lansky A. Zechel C. Angew. Chem., Int. Ed. Engl. 1996, 35: 2288 2a Oikawa M. Tanaka T. Kusomoto S. Sasaki M. Tetrahedron Lett. 2004, 45: 787 2b Swamy KMK. Yeh WB. Lin MJ. Sun CM. Curr. Med. Chem. 2003, 10: 2403 2c Sun CM. Swamy KMK. Lin MJ. Yeh WB. Chen FY. Tseng WH. Comb. Chem. High Throughput Screening 2003, 6: 133 2d Gravert DJ. Janda KD. Chem. Rev. 1997, 97: 489 2e Toy PH. Janda KD. Acc. Chem. Res. 2000, 33: 546 3a Lin XF. Zhang J. Wang YG. Tetrahedron Lett. 2003, 44: 4113 3b Lin XF. Zhang J. Cui SL. Wang YG. Synthesis 2003, 1569 3c Shang YJ. Wang YG. Tetrahedron Lett. 2002, 43: 2247 3d Shang YJ. Wang YG. Chin. J. Chem. 2003, 21: 7 3e Xia M. Wang YG. Tetrahedron Lett. 2002, 43: 7703 3f Chen CP. Chen YJ. Tetrahedron Lett. 2004, 45: 113 3g Cheng MF. Fang JM. J. Comb. Chem. 2004, 6: 99 3h Tung CL. Sun CM. Tetrahedron Lett. 2004, 45: 1159 4a Magriotis PA. Angew. Chem. Int. Ed. 2001, 40: 4377 4b Ojima I. Acc. Chem. Res. 1995, 28: 283 4c Ojima I. Delaloge F. Chem. Soc. Rev. 1997, 26: 377 5 Synthesis of beta-Lactam Antibiotics: Chemistry, Biocatalysis and Process Integration Bruggink A. Kluwer; Dordrecht: 2001. 6 Bonneau PR. Hasani F. Plouffe C. Malenfant E. LaPlante SR. Guse I. Ogilvie WW. Plante R. Davidson WC. Hopkins JL. Morelock MM. Cordingley MG. Deziel R. J. Am. Chem. Soc. 1999, 121: 2965 7 Annunziata R. Benaglia M. Cinquini M. Cozzi Puglisi FA. Bioorg. Med. Chem. 2002, 10: 1813 8 Han WT. Trehan AK. Wright JJK. Federici ME. Seiler SM. Meanwell NA. Bioorg. Med. Chem. 1995, 3: 1123 9 Firestone RA. Barker PL. Pisano JM. Ashe BM. Dahlgren ME. Tetrahedron 1990, 46: 2255 10 Jian SZ. Wang YG. Chem. Lett. 2004, 33: 866 11 Shang YJ. Shou WG. Wang YG. Synlett 2003, 1064 12 Auxiliary 5 was prepared by the method described by: Kondo K. Seki M. Kuroda T. Yamanaka T. Iwasaki T. J. Org. Chem. 1997, 62: 2877 See for example: 13a Townes JA. Evans MA. Queffelec J. Taylor SJ. Morken JP. Org. Lett. 2002, 4: 2537 13b Chen L. Zhao G. Ding Y. Tetrahedron Lett. 2003, 44: 2611 14 Kirschning A. Monenschein H. Wittenberg R. Chem. Eur. J. 2000, 6: 4445 15a Nagao Y. Kumagai T. Tamai S. Abe T. Kuramoto Y. Taga T. Aoyagi S. Nagase Y. Ochiai M. Inoue Y. Fujita E. J. Am. Chem. Soc. 1986, 108: 4673 15b Fuentes LM. Shinkai I. Saltsmann TN. J. Am. Chem. Soc. 1986, 108: 4675 15c Ito Y. Sasaki A. Tamoto K. Sunagawa M. Terashima S. Tetrahedron 1991, 47: 2801 15d Nagao Y. Nagase Y. Kumagai T. Matsunaga H. Abe T. Shimada O. Hayashi T. Inoue Y. J. Org. Chem. 1992, 57: 4243 15e Fukuzawa S. Matsuzawa H. Yoshimitsu S. J. Org. Chem. 2000, 65: 1702 16 Jian SZ. Ma C. Wang YG. Synthesis 2005, 725
