Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Improved Robust Method for Preparing Optically Active 3-Alkyl-3-phenyl-1,4-dioxane-2,5-diones; A Promising New Chiral Template Ryohei Nagase, Yuuki Iida, Mikiko Sugi, Tomonori Misaki, Yoo Tanabe*Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyougo 669-1337, JapanFax: +81(79)5659077; e-Mail: tanabe@kwansei.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract A robust method for preparing (3S)-3-alkyl-3-phenyl-1,4-dioxane-2,5-diones was developed using an improved cyclocondensation reaction between (S)-α-alkylmandelic acids and 2-bromocarbonyl halides. Subtle differences in the reaction conditions, including separate additions of triethylamine, significantly increased the yield compared with Schöllkopf’s original method. Key words 1,4-dioxan-2,5-diones - cyclocondensation - α-alkylmandelic acids - chiral template Full Text References References 1 Guillarumet G. Comprehensive Heterocyclic Chemistry II Vol. 6: Katritzky AR. Rees CW. Scriven EF. Pergamon; Oxford: 1996. p.447 2 Schöllkopf VU. Hartwig W. Sprotte U. Jung W. Angew. Chem., Int. Ed. Engl. 1979, 18: 310 3a Coates GW. Moore DR. Angew. Chem. Int. Ed. 2004, 43: 2215 3b Dechy-Cabaret O. Martin-Vaca B. Bourissou D. Chem. Rev. 2004, 104: 6147 4 Kumar PR, Murthy KN, Raju S, Sarma MR, Reddy GO, and Venkateswarlu A. inventors; WO 03010157, . ; Chem. Abstr. 2003, 138, 137316 5 Misaki T. Ureshino S. Nagase R. Oguni Y. Tanabe Y. Org. Process Res. Dev. 2006, 10: 500 6a Seebach D. Naef R. Helv. Chim. Acta 1981, 64: 2704 6b Fráter G. Müller U. Günther W. Tetrahedron Lett. 1981, 22: 4221 6c Seebach D. Sting AR. Hoffmann M. Angew. Chem., Int. Ed. Engl. 1996, 35: 2708 6d Clayden J. Greeves N. Warren S. Wothers P. Organic Chemistry Oxford University Press; New York: 2001. p.855 7a Nagase R. Oguni Y. Misaki T. Tanabe Y. Synthesis 2006, 3915 For related studies of stereocomplementary cyclocondensation reaction for preparing thiazolidine-4-ones, see: 7b Tanabe Y. Suzukamo G. Komuro Y. Imanishi N. Morooka S. Enomoto M. Kojima A. Sanemitsu Y. Mizutani M. Tetrahedron Lett. 1991, 32: 379 7c Tanabe Y. Kubota Y. Sanemitsu Y. Itaya N. Suzukamo G. Tetrahedron Lett. 1991, 32: 383 7d Tanabe Y. Yamamoto H. Murakami M. Yanagi K. Kubota Y. Okumura H. Sanemitsu Y. Suzukamo G. J. Chem. Soc., Perkin Trans. 1 1995, 935 8 Direct formation of 5B from (S)-4a (not through 5A) might be considered. However, we speculate that this reaction does not proceed because carboxylate anion of (S)-4a has higher reactivity than the tertiary hydroxy group. 9a Chang J.-W. Jang D.-P. Uang B.-J. Liao F.-L. Wang S.-L. Org. Lett. 1999, 1: 2061 9b Ooi T. Fukumoto K. Maruoka K. Angew. Chem. Int. Ed. 2006, 45: 3839
