General Method for the Synthesis of Chiral 2,3-Bisarylmethoxy-1,4-Butanediols from l-(+)-Tartrate

Riichiro Tsuji; Shigeru Arai; Atsushi Nishida

doi:10.1055/s-2004-815997

FEATUREARTICLE

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, Japan
Fax: +81(43)2902909; e-Mail: nishida@p.chiba-u.ac.jp;

Abstract

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

<A NAME="RF11603SS-1">1</A> Morrison JD. Scott AI. Asymmetric Synthesis Vol. 4: Academic Press Inc.; New York: 1984. p.1

<A NAME="RF11603SS-2">2</A> Liu W. Szewczyk JM. Waykole L. Repic O. Blacklock TJ. Tetrahedron Lett. 2002, 43: 1373

<A NAME="RF11603SS-3A">3a</A> Flores-Santos L. Martin E. Diéguez M.-B. Claver C. Tetrahedron: Asymmetry 2001, 12: 3029

<A NAME="RF11603SS-3B">3b</A> Gonsalves AMd’AR. Bayon JC. Pereira MM. Serra MES. Pereira JPR. J. Organomet. Chem. 1998, 553: 199

<A NAME="RF11603SS-3C">3c</A> Cunningham AF. Kündig EP. J. Org. Chem. 1988, 53: 1823

<A NAME="RF11603SS-4A">4a</A> Arai S. Tsuji R. Nishida A. Tetrahedron Lett. 2002, 43: 9535

Unpublished result

<A NAME="RF11603SS-4C">4c</A> Shibuguchi T. Fukuta Y. Akachi Y. Sekine A. Ohshima T. Shibasaki M. Tetrahedron Lett. 2002, 43: 9539

<A NAME="RF11603SS-5A">5a</A> Kalinowski H. Crass G. Seebach D. Chem. Ber. 1981, 114: 477

<A NAME="RF11603SS-5B">5b</A> Nemoto H. Takamatsu S. Yamamoto Y. J. Org. Chem. 1991, 56: 1321

<A NAME="RF11603SS-6A">6a</A> Rubin LJ. Lardy HA. Fischer HOL. J. Am. Chem. Soc. 1952, 74: 425

<A NAME="RF11603SS-6B">6b</A> Palomo C. Oiarbide M. Landa A. Esnal A. Linden A. J. Org. Chem. 2001, 66: 4180

<A NAME="RF11603SS-6C">6c</A> Inoue M. Fujimoto K. Furusyo M. Nakazumi H. J. Am. Chem. Soc. 1999, 121: 1452

<A NAME="RF11603SS-7">7</A> Thomas RM. Mohan GH. Iyenger DS. Tetrahedron Lett. 1997, 38: 4721

We assume hydroboration would proceed exclusively because no olefinic signals were observed in the ¹H NMR spectra of crude products.

<A NAME="RF11603SS-9">9</A> Vutukuri DR. Bharathi P. Yu Z. Rajasekaran K. Tran M.-H. Thayumanavan S. J. Org. Chem. 2003, 68: 1146