A simple, convenient preparation for enantiomerically pure 1,1′-bi-2-naphthols

被引：39
|
作者：
Shan, ZX [1 ]
Xiong, Y [1 ]
Li, WZ [1 ]
Zhao, DJ [1 ]
机构：
[1] Wuhan Univ, Dept Chem, Wuhan 430072, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 22期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/S0957-4166(98)00396-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A new preparative method for enantiomerically pure 1,1'-bi-2-naphthols is described. 1,1'-Bi-2-naphtholboric anhydride generated from the reaction of racemic 1,1'-bi-2-naphthol and boric acid in toluene is reacted with (S)-proline to produce 1,1'-bi-2-naphtholboric proline anhydride. Its two diastereomers were efficiently separated in THE After treating successively with NaOH, HCl, and recrystallizing from benzene, enantiomerically pure (S)and (R)-1,1'-bi-2-naphthol were obtained in 71-79% yield and in 62-74% yield, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3985 / 3989
页数：5
相关论文
共 50 条
  • [21] Liquid chromatographic resolution of 1,1′-bi-2-naphthol and 3,3′-diaryl-1,1′-bi-2-naphthols on pirkle-type chiral stationary phases based on leucine and phenylglycine
    Hyun, MH
    Kim, KS
    Cho, YJ
    JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2005, 28 (04) : 527 - 535
  • [22] Decarboxylative Iodination and Suzuki-Miyaura Coupling Reactions to Access Chiral 3,3′-Diaryl-1,1′-bi-2-naphthols
    Karthick, Muthupandi
    Gupta, Sushmita
    Ramanathan, Chinnasamy Ramaraj
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 291 - 303
  • [23] EXPEDIENT ROUTE TO 3-SUBSTITUTED AND 3,3'-SUBSTITUTED 1,1'-BI-2-NAPHTHOLS BY DIRECTED ORTHO METALATION AND SUZUKI CROSS COUPLING METHODS
    COX, PJ
    WANG, W
    SNIECKUS, V
    TETRAHEDRON LETTERS, 1992, 33 (17) : 2253 - 2256
  • [24] Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: a chiral resolving agent for the resolution and absolute configuration assignment of 7,7′-disubstituted 1,1′-bi-2-naphthols
    Dolsophon, Kulvadee
    Ruangsupapichat, Nopporn
    Soponpong, Jakapun
    Sungsuwan, Suttipun
    Prabpai, Samran
    Kongsaeree, Palangpon
    Thongpanchang, Tienthong
    TETRAHEDRON-ASYMMETRY, 2016, 27 (22-23) : 1113 - 1120
  • [25] 1,1′-Binaphthyl-2,2′-diyl phosphoroselenoyl chloride as a chiral molecular tool for the preparation of enantiomerically pure alcohols and amines
    Murai, T
    Matsuoka, D
    Morishita, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) : 4584 - 4585
  • [26] CONVENIENT PREPARATION OF 2-BENZOXAZOLINONES WITH 1,1-CARBONYLDIIMIDAZOLE
    NACHMAN, RJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (06) : 1545 - 1547
  • [27] 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
  • [28] 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
  • [29] Convenient synthesis of 1-arylmethyl-2-naphthols
    Paul, Nawal K.
    Dietrich, Lindsay
    Jha, Amitabh
    SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) : 877 - 888
  • [30] A CONVENIENT METHOD FOR THE PREPARATION OF ENANTIOMERICALLY PURE 2-SUBSTITUTED N-TOSYLAZIRIDINES
    BERRY, MB
    CRAIG, D
    SYNLETT, 1992, (01) : 41 - 44
12345