A Rhodium IBiox[(-)-menthyl] Complex as a Highly Selective Catalyst for the Asymmetric Hydroarylation of Azabicyles: An Alternative Route to Epibatidine

被引：76

作者：

Bexrud, Jason ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

N-HETEROCYCLIC CARBENES; FRAGMENT-BASED APPROACH; ENANTIOSELECTIVE DESYMMETRIZATION; RESTRICTED FLEXIBILITY; LIGANDS; (+/-)-EPIBATIDINE; STABILITY; DESIGN; SALTS;

D O I：

10.1021/ol101067d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and characterization of a new chiral rhodium N-heterocyclic carbene complex, Rh(IBiox[(-)-menthyl](CO)(2)Cl, is reported. In addition, the very high enantioselectivity exhibited by this complex, as a catalyst for the asymmetric hydroarylation of azabicycles, is demonstrated and applied to the synthesis of epibatidine.

引用

页码：3160 / 3163

页数：4

共 45 条

[1] Enantioselective α-arylation of cyclohexanones with diaryl iodonium salts:: Application to the synthesis of (-)-epibatidine [J].

Aggarwal, VK ;

Olofsson, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5516-5519

[2] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201

[3] Aza-prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes:: Syntheses of (±)-epibatidine and (±)-epiboxidine [J].

Armstrong, Alan ;

Bhonoah, Yunas ;

Shanahan, Stephen E. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :8019-8024

[4] Synthesis and application of complexes of a novel chiral diphenylphosphino-functionalized N-heterocyclic carbene [J].

Bappert, E ;

Helmchen, G .

SYNLETT, 2004, (10) :1789-1793

[5] Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].

Batey, RA ;

Thadani, AN ;

Smil, DV .

ORGANIC LETTERS, 1999, 1 (10) :1683-1686

[6] Acceptor substituted N-heterocyclic carbenes and their Rh(I) complexes:: Synthesis, structure and properties [J].

Bittermann, Agnes ;

Haerter, Peter ;

Herdtweck, Eberhardt ;

Hoffmann, Stephan D. ;

Herrmann, Wolfgang A. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (12) :2079-2090

[7] Stereoselective Transformations of meso Bicyclic Hydrazines: Versatile Access to Functionalized Aminocyclopentanes [J].

Bournaud, Chloee ;

Chung, Florence ;

Luna, Alejandro Perez ;

Pasco, Morgane ;

Errasti, Gauthier ;

Lecourt, Thomas ;

Micouin, Laurent .

SYNTHESIS-STUTTGART, 2009, (06) :869-887

[8] TOTAL SYNTHESIS OF EPIBATIDINE [J].

BROKA, CA .

TETRAHEDRON LETTERS, 1993, 34 (20) :3251-3254

[9] EPIBATIDINE ANALOGS SYNTHESIZED FOR CHARACTERIZATION OF NICOTINIC PHARMACOPHORES-A REVIEW [J].

Carroll, F. Ivy .

HETEROCYCLES, 2009, 79 :99-120

[10] Epibatidine structure-activity relationships [J].

Carroll, FI .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (08) :1889-1896

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