A Convenient Synthesis of (S)-H4-BINOL and Its Derivatives via Hydrogenation of Monoesters of BINOL

被引：4

作者：

Li, Xinsheng ^{[1
]}

Ding, Qianchang ^{[1
]}

Ge, Jianfeng ^{[2
]}

Xie, Jianwu ^{[1
]}

Xu, Dongcheng ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Zhejiang Key Lab React Chem Solid Surfaces, Jinhua 321004, Peoples R China

[2] Suzhou Univ, Dept Mat & Engn, Suzhou 215006, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期

关键词：

DIELS-ALDER REACTION; ENANTIOSELECTIVE ADDITION; ASYMMETRIC CATALYSIS; AROMATIC-ALDEHYDES; 1,1'-BINAPHTHYLS; REDUCTION; LIGANDS; 5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL; DIETHYLZINC; COMPLEXES;

D O I：

10.1021/jo802542m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new multigram synthesis of chiral (S)-H-4-BINOL and its derivatives in moderate to high yield (up to 83% total yield) via monoesterification of (S)-BINOL, hydrogenation, and saponification reaction was described. The two new monomethylated (S)-H-4-BINOL obtained may be useful materials in asymmetric catalysis.

引用

页码：1785 / 1787

页数：3

共 19 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2] BINOL: A versatile chiral reagent [J].

Brunel, JM .

CHEMICAL REVIEWS, 2005, 105 (03) :857-897

[3] 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

[4] Modified BINOL ligands in asymmetric catalysis [J].

Chen, Y ;

Yekta, S ;

Yudin, AK .

CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211

[5] HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS [J].

CRAM, DJ ;

HELGESON, RC ;

PEACOCK, SC ;

KAPLAN, LJ ;

DOMEIER, LA ;

MOREAU, P ;

KOGA, K ;

MAYER, JM ;

CHAO, Y ;

SIEGEL, MG ;

HOFFMAN, DH ;

SOGAH, GDY .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1930-1946

[6] Reduction of 1,1′-binaphthyls to octahydro-1,1′-binaphthyl derivatives with Raney Ni-Al alloy in aqueous solution [J].

Guo, H ;

Ding, KL .

TETRAHEDRON LETTERS, 2000, 41 (51) :10061-10064

[7] A new method for the synthesis of H4-BINOL [J].

Heumann, Lars V. ;

Keck, Gary E. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4725-4727

[8] Convenient and efficient reduction of 1,1′-binaphthyls to H8-1,1′-binaphthyl derivatives with Pd and Ru catalysts on solid support [J].

Korostylev, A ;

Tararov, VI ;

Fischer, C ;

Monsees, A ;

Börner, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3220-3221

[9] Highly enantioselective hydrogenation of enamides catalyzed by rhodium-monodentate phosphoramidite complex derived from H8-BINOL [J].

Li, XS ;

Jia, X ;

Lu, G ;

Au-Yeung, TTL ;

Lam, KH ;

Lo, TWH ;

Chan, ASC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2687-2691

[10] Enantioselective borane reduction of aromatic ketones using chiral BINOL derivatives as ligands in an aluminum catalyst [J].

Lin, YM ;

Fu, IP ;

Uang, BJ .

TETRAHEDRON-ASYMMETRY, 2001, 12 (23) :3217-3221

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