Full Text:   <1713>

CLC number: O621.14+4

On-line Access: 

Received: 2000-10-07

Revision Accepted: 2001-01-02

Crosschecked: 0000-00-00

Cited: 1

Clicked: 3493

Citations:  Bibtex RefMan EndNote GB/T7714

-   Go to

Article info.
1. Reference List
Open peer comments

Journal of Zhejiang University SCIENCE A 2001 Vol.2 No.3 P.275-277

http://doi.org/10.1631/jzus.2001.0275


A SIMPLE METHOD FOR CHIRAL RESOLUTION OF 1,1'-BI-2-NAPHTHOL


Author(s):  LI Xiao-tao, JIANG Guang-guang, CHEN Wei-xiang, XU Zhu-de

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Corresponding email(s): 

Key Words:  1, 1'-bi-2-naphthol, chiral resolution


Share this article to: More

LI Xiao-tao, JIANG Guang-guang, CHEN Wei-xiang, XU Zhu-de. A SIMPLE METHOD FOR CHIRAL RESOLUTION OF 1,1'-BI-2-NAPHTHOL[J]. Journal of Zhejiang University Science A, 2001, 2(3): 275-277.

@article{title="A SIMPLE METHOD FOR CHIRAL RESOLUTION OF 1,1'-BI-2-NAPHTHOL",
author="LI Xiao-tao, JIANG Guang-guang, CHEN Wei-xiang, XU Zhu-de",
journal="Journal of Zhejiang University Science A",
volume="2",
number="3",
pages="275-277",
year="2001",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2001.0275"
}

%0 Journal Article
%T A SIMPLE METHOD FOR CHIRAL RESOLUTION OF 1,1'-BI-2-NAPHTHOL
%A LI Xiao-tao
%A JIANG Guang-guang
%A CHEN Wei-xiang
%A XU Zhu-de
%J Journal of Zhejiang University SCIENCE A
%V 2
%N 3
%P 275-277
%@ 1869-1951
%D 2001
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2001.0275

TY - JOUR
T1 - A SIMPLE METHOD FOR CHIRAL RESOLUTION OF 1,1'-BI-2-NAPHTHOL
A1 - LI Xiao-tao
A1 - JIANG Guang-guang
A1 - CHEN Wei-xiang
A1 - XU Zhu-de
J0 - Journal of Zhejiang University Science A
VL - 2
IS - 3
SP - 275
EP - 277
%@ 1869-1951
Y1 - 2001
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2001.0275


Abstract: 
An improved method for preparing enantiomerically pure 1,1'-bi-2-naphthols is described. 1,1'-bi-2-naphthol boric anhydride was generated from the reaction of racemic 1,1'-bi-2-naphthol and boric anhydride. Its two diastereoisomers could be efficiently separated in THF using (L)-proline as the resolving agent. Treatment in three successive steps yielded 79% and 74% enantiomerically pure (S)- and (R)-1,1'-bi-2-naphthol respectively.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

[1] Gong Baoqing, Chen Wanyi, 1991. A new and efficient method for the resolution of 2,2'-dihydroxy-1,1'-binaphthyl. J. Org. Chem., 56: 423-425.

[2] Hu Qiaosheng, Vitharana, D., 1995. An efficient and practical direct resolution of racemic 1,1'-bi-2-naphthol to both of its pure enantiomers. Tetrahedron: Asymmetry, 6:2123-2126.

[3] Periasamy, M., Prasad, A. S. B., 1995. A simple convenient method for the resolution of racemic 2,2'-dihydroxy-1,1'-binaphthyl using (s)-proline. Tetrahedron: Asymmetry, 6:341-344.

[4] Periasamy, M., Venkatraman, L., 1997. New method of resolution and enrichment of enantiomeric excess of 1,1'-bi-2-naphthol. J. Org. Chem., 62:4302-4306.

[5] Shan Zixing, Cheng Fuyong, 1997. An improved approach to (r)-(+)-1,1'-bi-2-naphthol of 100% enantiomeric excess via a cyclic borate ester. Tetrahedron: Asymmetry, 8:1175-1177.

[6] Shan Zixing, Wang Guoping, 1996. Preparation of enantiomerically pure 1,1'-bi-2-naphthol via cyclic borate ester. Tetrahedron: Asymmetry, 7:2847-2850.

[7] Shan Zixing, Xiong Ying, 1999. Resolution of racemic 1,1'-bi-2-naphthol using (s)-proline via a cyclic borate ester. Tetrahedron, 55:3893-3896.

[8] Toda, F., Tanaka, K., 1988. Efficient optical resolution of 2,2'-dihydroxy-1,1'-binaphthyl and related compounds by complex formation with novel chiral host compounds derived from tartaric acid. J. Org. Chem., 53:3607-3609.

[9] Venkatraman, L., Periasamy, M., 1996. A novel, simple method for enrichment of enantiomeric excess of scalemic 1,1'-bi-2-naphthol. Tetrahedron: Asymmetry, 7:2471-2474

Open peer comments: Debate/Discuss/Question/Opinion

<1>

Please provide your name, email address and a comment





Journal of Zhejiang University-SCIENCE, 38 Zheda Road, Hangzhou 310027, China
Tel: +86-571-87952783; E-mail: cjzhang@zju.edu.cn
Copyright © 2000 - 2022 Journal of Zhejiang University-SCIENCE