Synthesis, Table of Contents FEATUREARTICLE © Georg Thieme Verlag Stuttgart · New York General Method for the Synthesis of Chiral 2,3-Bisarylmethoxy-1,4-Butanediols from l-(+)-Tartrate Riichiro Tsuji, Shigeru Arai, Atsushi Nishida*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, JapanFax: +81(43)2902909; e-Mail: nishida@p.chiba-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract Various (2S,3S)-2,3-bisarylmethoxy-1,4-butanediols 3a-h were synthesized from l-(+)-tartrate through bisallylether 12. Protection of the primary alcohol as an allyl ether was essential for selective deprotection in the presence of reactive arylmethyl ethers. Key words tartaric acid - allyl ether - catalyst - palladium - deprotection Full Text References References 1 Morrison JD. Scott AI. Asymmetric Synthesis Vol. 4: Academic Press Inc.; New York: 1984. p.1 2 Liu W. Szewczyk JM. Waykole L. Repic O. Blacklock TJ. Tetrahedron Lett. 2002, 43: 1373 3a Flores-Santos L. Martin E. Diéguez M.-B. Claver C. Tetrahedron: Asymmetry 2001, 12: 3029 3b Gonsalves AMd’AR. Bayon JC. Pereira MM. Serra MES. Pereira JPR. J. Organomet. Chem. 1998, 553: 199 3c Cunningham AF. Kündig EP. J. Org. Chem. 1988, 53: 1823 4a Arai S. Tsuji R. Nishida A. Tetrahedron Lett. 2002, 43: 9535 4b Unpublished result 4c Shibuguchi T. Fukuta Y. Akachi Y. Sekine A. Ohshima T. Shibasaki M. Tetrahedron Lett. 2002, 43: 9539 5a Kalinowski H. Crass G. Seebach D. Chem. Ber. 1981, 114: 477 5b Nemoto H. Takamatsu S. Yamamoto Y. J. Org. Chem. 1991, 56: 1321 6a Rubin LJ. Lardy HA. Fischer HOL. J. Am. Chem. Soc. 1952, 74: 425 6b Palomo C. Oiarbide M. Landa A. Esnal A. Linden A. J. Org. Chem. 2001, 66: 4180 6c Inoue M. Fujimoto K. Furusyo M. Nakazumi H. J. Am. Chem. Soc. 1999, 121: 1452 7 Thomas RM. Mohan GH. Iyenger DS. Tetrahedron Lett. 1997, 38: 4721 8 We assume hydroboration would proceed exclusively because no olefinic signals were observed in the 1H NMR spectra of crude products. 9 Vutukuri DR. Bharathi P. Yu Z. Rajasekaran K. Tran M.-H. Thayumanavan S. J. Org. Chem. 2003, 68: 1146