Resolution of racemic 1,1′-bi-2-naphthol using (S)-proline via a cyclic borate ester

被引：32
|
作者：
Shan, ZX [1 ]
Xiong, Y [1 ]
Zhao, DJ [1 ]
机构：
[1] Wuhan Univ, Dept Chem, Wuhan 430072, Peoples R China
来源：
TETRAHEDRON | 1999年 / 55卷 / 13期
基金：
中国国家自然科学基金;
关键词：
resolution; 1,1 '-bi-2-naphthol; (S)-proline; cyclic borate ester;
D O I：
10.1016/S0040-4020(99)00085-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,1'-Bi-2-naphtholborane generated from racemic 1,1'-bi-2-naphthol and borane dimethyl sulfide complex reacted with (S)-proline in tetrahydrofuran to form a spirocyclic 1,1'-bi-2-naphtholboric proline anhydride. Its two diastereoisomers could be separated efficiently under the experimental conditions, from which enantiomerically pure (R)-(+)- and (S)-(-)-1,1'-bi-2-naphthol were obtained in ca. 80% overall yield, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3893 / 3896
页数：4
相关论文
共 50 条
  • [1] Preparation of enantiomerically pure 1,1'-bi-2-naphthol via cyclic borate ester
    Shan, ZX
    Wang, GP
    Duan, B
    Zhao, DJ
    TETRAHEDRON-ASYMMETRY, 1996, 7 (10) : 2847 - 2850
  • [2] An improved approach to (R)-(+)-1,1'-bi-2-naphthol of 100% enantiomeric excess via a cyclic borate ester
    Shan, ZX
    Cheng, FY
    Huang, SW
    Zhao, DJ
    Jing, ZZ
    TETRAHEDRON-ASYMMETRY, 1997, 8 (08) : 1175 - 1177
  • [3] Resolution of 1,1′-bi-2-naphthol
    Cai, DW
    Hughes, DL
    Verhoeven, TR
    Reider, PJ
    ORGANIC SYNTHESES, VOL 76 - 1999, 1999, 76 : 1 - 5
  • [4] Racemic 1,1′-bi-2-naphthol dimethylformamide sesquisolvate:: a redetermination
    Yuan, JX
    Song, XY
    Ng, SW
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O3457 - O3458
  • [5] Crystal engineering of chiral superstructures based on (R)-(+)-1,1′-bi-2-naphthol and the alkali derivatives of racemic (R,S)-1,1′-bi-2-naphthol
    Grepioni, F
    Gladiali, S
    Scaccianoce, L
    Ribeiro, P
    Braga, D
    NEW JOURNAL OF CHEMISTRY, 2001, 25 (05) : 690 - 695
  • [6] SIMPLE AND EFFICIENT RESOLUTION OF 1,1'-BI-2-NAPHTHOL
    CAI, DW
    HUGHES, DL
    VERHOEVEN, TR
    REIDER, PJ
    TETRAHEDRON LETTERS, 1995, 36 (44) : 7991 - 7994
  • [7] Simple and efficient resolution of 1,1'-bi-2-naphthol
    Cai, DW
    Hughes, DL
    Verhoeven, TR
    Reider, PJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 299 - ORGN
  • [8] A new, convenient method of resolution of racemic 1,1′-bi-2-naphthol using boric acid and (R)-(+)-α-methylbenzylamine
    Periasamy, M
    Venkatraman, L
    Sivakumar, S
    Sampathkumar, N
    Ramanathan, CR
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20): : 7643 - 7645
  • [9] A SIMPLE METHOD FOR CHIRAL RESOLUTION OF 1,1'-BI-2-NAPHTHOL
    李晓桃
    蒋珖珖
    陈卫祥
    徐铸德
    Journal of Zhejiang University-Science A(Applied Physics & Engineering), 2001, (03) : 36 - 38
  • [10] (S)-(-)-1,1′-bi-2-naphthol dimethylformamide sesquisolvate
    Yuan, JX
    Song, XY
    Ng, SW
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O3459 - O3460
12345