Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization

被引：60

作者：

Giri, Ramesh ^{[1
]}

Wasa, Masayuki ^{[1
]}

Breazzano, Steven P. ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 25期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ol0618858

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

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页码：5685 / 5688

页数：4

相关论文

共 43 条

[1] Diastereoselective synthesis of cyclopropane amino acids using diazo compounds generated in situ [J].

Adams, LA ;

Aggarwal, VK ;

Bonnert, RV ;

Bressel, B ;

Cox, RJ ;

Shepherd, J ;

de Vicente, J ;

Walter, M ;

Whittingham, WG ;

Winn, CL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9433-9440

[2] REACTIONS OF TERT-BUTYLLITHIUM WITH ALPHA,OMEGA-DIHALOALKANES - EVIDENCE FOR SINGLE-ELECTRON-TRANSFER-MEDIATED METAL-HALOGEN INTERCHANGE INVOLVING ALKYL RADICAL-HALIDE ION ADDUCTS [J].

BAILEY, WF ;

GAGNIER, RP ;

PATRICIA, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2098-2107

[3] First intermolecular cyclopropanation of Fischer dialkylaminocarbene complexes.: Synthesis of 1-aminocyclopropanecarboxylic acid derivatives [J].

Barluenga, J ;

Aznar, F ;

Gutiérrez, I ;

García-Granda, S ;

Llorca-Baragaño, MA .

ORGANIC LETTERS, 2002, 4 (24) :4273-4276

[4] Synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) derivatives:: Key intermediates for the preparation of inhibitors of the hepatitis C virus NS3 protease [J].

Beaulieu, PL ;

Gillard, J ;

Bailey, MD ;

Boucher, C ;

Duceppe, JS ;

Simoneau, B ;

Wang, XJ ;

Zhang, L ;

Grozinger, K ;

Houpis, I ;

Farina, V ;

Heimroth, H ;

Krueger, T ;

Schnaubelt, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15) :5869-5879

[5]

CAMBIE RC, 1978, J CHEM SOC P1, V12, P1483

[6] ALKOXYL RADICALS FROM ALCOHOLS SPECTROSCOPIC DETECTION OF INTERMEDIATE ALKYL AND ACYL HYPOIODITES IN THE SUAREZ AND BEEBE REACTIONS [J].

COURTNEIDGE, JL ;

LUSZTYK, J ;

PAGE, D .

TETRAHEDRON LETTERS, 1994, 35 (07) :1003-1006

[7] Formation of cyclopropanes by holmolytic substitution reactions of 3-iodopropyl radicals: Preparative and rate studies [J].

Curran, DP ;

Gabarda, AE .

TETRAHEDRON, 1999, 55 (11) :3327-3336

[8] Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors [J].

Devreux, V ;

Wiesner, J ;

Goeman, JL ;

Van der Eycken, J ;

Jomaa, H ;

Van Calenbergh, S .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (08) :2656-2660

[9] Recent advances in asymmetric catalytic metal carbene transformations [J].

Doyle, MP ;

Forbes, DC .

CHEMICAL REVIEWS, 1998, 98 (02) :911-935

[10] New aspects of catalytic asymmetric cyclopropanation [J].

Doyle, MP ;

Protopopova, MN .

TETRAHEDRON, 1998, 54 (28) :7919-7946

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