Synthesis and structure of chiral (R)-2,2′-bis-silyl-substituted 1,1′-binaphthyl derivatives

被引：18

作者：

Hoshi, T

Shionoiri, H

Suzuki, T

Ando, M

Hagiwara, H

机构：

[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan

[2] Niigata Univ, Fac Engn, Niigata 9502181, Japan

来源：

CHEMISTRY LETTERS | 1999年 / 11期

关键词：

D O I：

10.1246/cl.1999.1245

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

First synthesis of optically active 2,2'-bis-silyl-substituted 1,1'-binaphthyl derivatives, (R)-(+)-2,2'-bis(trimethylsilyl)-1,1'-binaphthyl ((R)-(+)-1) and (R)-(-)-2,2'-bis(dimethylphenylsilyl)-1,1'-binaphthyl ((R)-(-)-2), has been accomplished by the direct bis-silylation of chiral 2,2'-dibromo-1,1'-binaphthyl (DBBN). The molecular structure and the absolute configuration of (R)-(-)2 have been determined by means of X-ray crystallography.

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页码：1245 / 1246

页数：2

相关论文

共 11 条

[1] o-bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu4NF catalyst [J].

Asao, N ;

Shibato, A ;

Itagaki, Y ;

Jourdan, F ;

Maruoka, K .

TETRAHEDRON LETTERS, 1998, 39 (20) :3177-3180

[2] Synthesis and dynamic behavior of the heptafluorotrisilacyclohexane anion: A new fluxional silicate with rapid intramolecular exchange of fluoride ligand [J].

Brondani, D ;

Carre, FH ;

Corriu, RJP ;

Moreau, JJE ;

Man, MWC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (03) :324-326

[3] PREPARATION AND LITHIATION OF OPTICALLY-ACTIVE 2,2'-DIHALO-1,1'-BINAPHTHYLS - A GENERAL STRATEGY FOR OBTAINING CHIRAL, BIDENTATE LIGANDS FOR USE IN ASYMMETRIC-SYNTHESIS [J].

BROWN, KJ ;

BERRY, MS ;

WATERMAN, KC ;

LINGENFELTER, D ;

MURDOCH, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :4717-4723

[4] Synthesis and chemistry of 2,2'-bis-silyl-substituted 1,1'-binaphthyl derivatives [J].

Fabris, F ;

DeLucchi, O .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 509 (01) :15-18

[5] Synchronized fluorine exchange with ring inversion of pentafluoro-1,4-disilacyclohexane anion [J].

Hoshi, T ;

Takahashi, M ;

Kira, M .

CHEMISTRY LETTERS, 1996, (08) :683-684

[6] SYNTHESIS AND CHEMISTRY OF NOVEL 2,2'-BINAPHTHYL-SUBSTITUTED ORGANOTIN LEWIS-ACIDS [J].

KRISHNAMURTI, R ;

KUIVILA, HG ;

SHAIK, NS ;

ZUBIETA, J .

ORGANOMETALLICS, 1991, 10 (02) :423-431

[7] Synthesis and structure of 2,2'-boryl-, germyl-, silyl-, and stannyl-substituted 1,1'-binaphthyl systems [J].

Schilling, B ;

Kaiser, V ;

Kaufmann, DE .

CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (07) :923-932

[8] PRACTICAL SYNTHESIS OF (R)-2,2' OR (S)-2,2'-BIS(DIARYLPHOSPHINO)-1,1'-BINAPHTHYLS (BINAPS) [J].

TAKAYA, H ;

MASHIMA, K ;

KOYANO, K ;

YAGI, M ;

KUMOBAYASHI, H ;

TAKETOMI, T ;

AKUTAGAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :629-635

[9] NOVEL PENTACOORDINATE ANIONIC SILICATE, [ORTHO-C6H4(SIPHF2)2F]-,K+.18-CROWN-6, CONTAINING A BENT FLUORIDE BRIDGE BETWEEN 2 SILICON ATOMS [J].

TAMAO, K ;

HAYASHI, T ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2422-2424

[10] Anion complexation by bidentate Lewis acidic hosts, ortho-bis(fluorosilyl) benzenes [J].

Tamao, K ;

Hayashi, T ;

Ito, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 506 (1-2) :85-91