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.

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页码：3985 / 3989

页数：5

相关论文

共 18 条

[1] Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes [J].

Bougauchi, M ;

Watanabe, S ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2329-2330

[2] Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes [J].

Chan, ASC ;

Zhang, FY ;

Yip, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :4080-4081

[3] ASYMMETRIC AZA-DIELS-ALDER REACTION MEDIATED BY CHIRAL BORON REAGENT [J].

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3264-3265

[4] Asymmetric hydroformylation of conjugated dienes catalyzed by chiral phosphine-phosphite-Rh(I) complex [J].

Horiuchi, T ;

Ohta, T ;

Shirakawa, E ;

Nozaki, K ;

Takaya, H .

TETRAHEDRON, 1997, 53 (23) :7795-7804

[5] Catalytic asymmetric aza Diels-Alder reactions using a chiral lanthanide Lewis acid. Enantioselective synthesis of tetrahydroquinoline derivatives using a catalytic amount of a chiral source [J].

Ishitani, H ;

Kobayashi, S .

TETRAHEDRON LETTERS, 1996, 37 (41) :7357-7360

[6] CATALYTIC ASYMMETRIC DIELS-ALDER REACTIONS [J].

KAGAN, HB ;

RIANT, O .

CHEMICAL REVIEWS, 1992, 92 (05) :1007-1019

[7]

KOBAYASHI S, 1994, CHEM LETT, V97, P1

[8] CATALYTIC ASYMMETRIC OXIDATION OF SULFIDES TO SULFOXIDES WITH TERT-BUTYL HYDROPEROXIDE USING BINAPHTHOL AS A CHIRAL AUXILIARY [J].

KOMATSU, N ;

HASHIZUME, M ;

SUGITA, T ;

UEMURA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4529-4533

[9] Asymmetric carbonyl addition reactions to benzyloxyaldehydes by binaphthol-titanium catalyst: Anti- vs. syn-diastereofacial preference in anomalous nonchelation complexation [J].

Mikami, K ;

Matsukawa, S ;

Sawa, E ;

Harada, A ;

Koga, N .

TETRAHEDRON LETTERS, 1997, 38 (11) :1951-1954

[10] CHEMICAL MULTIPLICATION OF CHIRALITY - SCIENCE AND APPLICATIONS [J].

NOYORI, R .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (02) :187-208