Catalytic asymmetric synthesis of 1,1′-spirobi[indan-3,3′-dione] via a double intramolecular C-H insertion process

被引：78

作者：

Takahashi, T ^{[1
]}

Tsutsui, H ^{[1
]}

Tamura, M ^{[1
]}

Kitagaki, S ^{[1
]}

Nakajima, M ^{[1
]}

Hashimoto, S ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 17期

关键词：

D O I：

10.1039/b103747c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient one-pot construction of optically active 1,1 ' -spirobi[indan-3,3 ' -dione] derivative (up to 80% ee) has been achieved by exploiting the double intramolecular C-H insertion reaction of dimethyl 2,2 ' -methylenebis(alpha -diazo-beta -oxobenzenepropanoate) under the influence of dirhodium (II) tetrakis[N-phthaloyl-(R or S)-tert-leucinate] as a catalyst.

引用

页码：1604 / 1605

页数：2

共 31 条

[1] Synthesis of spirosystems by rhodium(II)-carbenoid C-H insertion reactions. [J].

Aburel, PS ;

Undheim, K .

TETRAHEDRON LETTERS, 1998, 39 (22) :3813-3814

[2]

Anada M, 1999, SYNLETT, P1775

[3] Enantioselective intramolecular C-H insertion route to a key intermediate for the synthesis of trinem antibiotics [J].

Anada, M ;

Hashimoto, S .

TETRAHEDRON LETTERS, 1998, 39 (49) :9063-9066

[4] Enantioselective synthesis of 4-substituted 2-pyrrolidinones by site-selective C-H insertion of α-methoxycarbonyl-α-diazoacetanilides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] [J].

Anada, M ;

Hashimoto, S .

TETRAHEDRON LETTERS, 1998, 39 (1-2) :79-82

[5] Highly enantioselective construction of the key azetidin-2-ones for the synthesis of carbapenem antibiotics via intramolecular C-H insertion reactions of α-methoxycarbonyl-α-diazoacetamides catalysed by chiral dirhodium(II) carboxylates [J].

Anada, M ;

Watanabe, N ;

Hashimoto, S .

CHEMICAL COMMUNICATIONS, 1998, (15) :1517-1518

[6] Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands [J].

Arai, MA ;

Arai, T ;

Sasai, H .

ORGANIC LETTERS, 1999, 1 (11) :1795-1797

[7] 1,1′-spirobiindane-7,7′-diol:: a novel, C2-symmetric chiral ligand [J].

Birman, VB ;

Rheingold, AL ;

Lam, KC .

TETRAHEDRON-ASYMMETRY, 1999, 10 (01) :125-131

[8] ABSOLUTE CONFIGURATION AND CHIROPTICAL PROPERTIES OF OPTICALLY-ACTIVE 1,1'-SPIROBIINDAN, 1,1'-SPIROBIINDENE, AND 1,1'-SPIROBIINDANONE [J].

BREWSTER, JH ;

PRUDENCE, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (04) :1217-1229

[9] Novel spiro phosphinite ligands and their application in homogeneous catalytic hydrogenation reactions [J].

Chan, ASC ;

Hu, WH ;

Pai, CC ;

Lau, CP ;

Jiang, YZ ;

Mi, AQ ;

Yan, M ;

Sun, J ;

Lou, RL ;

Deng, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9570-9571

[10]

Davies H. M. L., 1997, ALDRICHIM ACTA, V30, P107

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