Asymmetric catalysis of the [5+2] cycloaddition reaction of vinylcyclopropanes and π-systems

被引：148

作者：

Wender, Paul A. ^{[1
]}

Haustedt, Lars O. ^{[1
]}

Lim, Jaehong ^{[1
]}

Love, Jennifer A. ^{[1
]}

Williams, Travis J. ^{[1
]}

Yoon, Joo-Yong ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem & Mol Pharmacol, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 19期

关键词：

D O I：

10.1021/ja058590u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As part of our studies of metal-catalyzed [m + n (+...o)] cycloadditions, we have previously reported the rhodium-catalyzed [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and π-systems. These studies have led to Rh(I) complexes that catalyze these reactions in minutes at room temperature or in water without organic solvents. We describe a comparative evaluation of several chiral catalysts for the [5 + 2] reaction, evaluation of a preferred catalyst, [((R)-BINAP)Rh]+SbF6-, with substrates differing in substitution and tether types - producing enantiomeric excesses ≥95% for several systems. A predictive model for the selectivity is also presented. Copyright © 2006 American Chemical Society.

引用

页码：6302 / 6303

页数：2

共 37 条

[1] Enantioselective syntheses of tremulenediol A and tremulenolide A [J].

Ashfeld, BL ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (20) :4535-4537

[2]

Evans F.J., 1986, NATURALLY OCCURRING

[3] HOMOGENEOUS CATALYSIS - CONVERSION OF 4-PENTENALS TO CYCLOPENTANONES BY EFFICIENT RHODIUM-CATALYZED HYDROACYLATION [J].

FAIRLIE, DP ;

BOSNICH, B .

ORGANOMETALLICS, 1988, 7 (04) :936-945

[4] Rhodium-catalyzed asymmetric [4+2] cycloisomerization reactions [J].

Gilbertson, SR ;

Hoge, GS ;

Genov, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :10077-10080

[5] Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions [J].

Gilbertson, SR ;

Hoge, GS .

TETRAHEDRON LETTERS, 1998, 39 (15) :2075-2078

[6] 8-oxabicyclo[3.2.1]oct-6-en-3-ones: Application to the asymmetric synthesis of polyoxygenated building blocks [J].

Hartung, IV ;

Hoffmann, HMR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (15) :1934-1949

[7]

Heath H, 2001, SYNTHESIS-STUTTGART, P2341

[8] NOVEL CYCLIZATION REACTIONS ON TRANSITION-METAL TEMPLATES - THE CATALYSIS OF INTRAMOLECULAR [4 + 2] CYCLOADDITIONS BY LOW VALENT RHODIUM COMPLEXES [J].

JOLLY, RS ;

LUEDTKE, G ;

SHEEHAN, D ;

LIVINGHOUSE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4965-4966

[9] Rhodium N-heterocyclic carbene-catalyzed [4+2] and [5+2] cycloaddition reactions [J].

Lee, SI ;

Park, Y ;

Park, JH ;

Jung, G ;

Choi, SY ;

Chung, YK ;

Lee, BY .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :91-96

[10] ON THE ASYMMETRIC RH(I) CATALYZED [4+2] CYCLOISOMERIZATION REACTION - ELECTRONIC AND TORSIONAL LIGAND CONTROL OF ABSOLUTE STEREOSELECTION [J].

MCKINSTRY, L ;

LIVINGHOUSE, T .

TETRAHEDRON, 1994, 50 (21) :6145-6154

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