KINETIC RESOLUTION OF 1,2-DIOLS USING NITROGEN-TETHERED BISIMIDAZOLINE-COPPER(I) CATALYZED BENZOYLATION

被引：6

作者：

Arai, Takayoshi ^{[1
]}

Mizukami, Tomoe ^{[1
]}

Mishiro, Asami ^{[1
]}

Yanagisawa, Akira ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

来源：

HETEROCYCLES | 2008年 / 76卷 / 02期

关键词：

Kinetic Resolution; Asymmetric Catalyst; 1,2-Diol; Imidazoline; Benzoylation;

D O I：

10.3987/COM-08-S(N)59

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrogen-tethered bisimidazoline (Nb-imidazoline) ligand was utilized in the Cu(I)-catalyzed benzoylation of 1,2-diols. With the assistance of i-Pr(2)NEt, the reaction of rac-1,2-diols with o-methylbenzoyl chloride was smoothly catalyzed by Nb-imidazoline-CuCl in CH(2)Cl(2) to give the corresponding o-methylbenzoylated secondary alcohols in tip to 79% ee.

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页码：995 / 1000

页数：6

相关论文

共 25 条

[1] Design and synthesis of a chiral N-tethered bis(imidazoline) ligand [J].

Arai, T ;

Mizukami, T ;

Yokoyama, N ;

Nakazato, D ;

Yanagisawa, A .

SYNLETT, 2005, (17) :2670-2672

[2] Reaction optimization using solid-phase catalysis-CD HTS:: Nb-imidazoline-Cu(I)-catalyzed asymmetric benzoylation of 1,2-diols [J].

Arai, Takayoshi ;

Mizukami, Tomoe ;

Yanagisawa, Akira .

ORGANIC LETTERS, 2007, 9 (06) :1145-1147

[3] Direct monitoring of the asymmetric induction of solid-phase catalysis using circular dichroism:: Diamine-CuI-catalyzed asymmetric Henry reaction [J].

Arai, Takayoshi ;

Watanabe, Masahiko ;

Fujiwara, Akitsugu ;

Yokoyama, Naota ;

Yanagisawa, Akira .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :5978-5981

[4] 2,3-dihydroimidazo[1,2-a]pyridines: A new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols [J].

Birman, VB ;

Uffman, EW ;

Hui, J ;

Li, XM ;

Kilbane, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12226-12227

[5] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[6] A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].

Evans, DA ;

Seidel, D ;

Rueping, M ;

Lam, HW ;

Shaw, JT ;

Downey, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693

[7] Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].

France, S ;

Guerin, DJ ;

Miller, SJ ;

Lectka, T .

CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012

[8] Enantioselective nucleophilic catalysis with "planar-chiral" heterocycles [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :412-420

[9] Cu(II)-aza(bisoxazoline)-catalyzed asymmetric benzoylations [J].

Gissibl, A ;

Finn, MG ;

Reiser, O .

ORGANIC LETTERS, 2005, 7 (12) :2325-2328

[10] ELECTRONIC PROPERTIES AND STEREOCHEMISTRY OF MONO-NUCLEAR COMPLEXES OF COPPER(II) ION [J].

HATHAWAY, BJ ;

BILLING, DE .

COORDINATION CHEMISTRY REVIEWS, 1970, 5 (02) :143-&