Chemodivergence in enantioselective desymmetrization of diazabicycles: Ring-opening versus reductive arylation

被引：99

作者：

Menard, Frederic ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 11期

关键词：

asymmetric catalysis; C-H activation; desymmetrization; rhodium; ring-opening reactions;

D O I：

10.1002/anie.200704708

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Divergent bicycle paths: A chemodivergent desymmetrization occurs after an initial enantioselective carbometalation step. The reaction brings a solution to the challenging problem of the enantioselective ring-opening of diazabicyclo-[2.2.1]heptanes to obtain arylated cyclopentenamines (see scheme, right). An alternative reaction pathway was discovered in which C-H insertion/1,4-metal migration occurs to give reductive arylation products (left). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2085 / 2088

页数：4

共 50 条

[1]

[Anonymous], 2007, ANGEW CHEM-GER EDIT

[2] The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines [J].

Arai, Kenzo ;

Lucarini, Simone ;

Salter, Matthew M. ;

Ohta, Kentaro ;

Yamashita, Yasuhiro ;

Kobayashi, Shuj .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) :8103-8111

[3] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[4] Highly active chiral ruthenium catalysts for asymmetric cross- and ring-opening cross metathesis [J].

Berlin, Jacob M. ;

Goldberg, Steven D. ;

Grubbs, Robert H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7591-7595

[5]

BERLIN JM, 2006, ANGEW CHEM, V118, P7753

[6] Rhodium-catalyzed asymmetric arylative ring opening of bicyclic hydrazines [J].

Bertolini, Ferruccio ;

Macchia, Franco ;

Pineschi, Mauro .

TETRAHEDRON LETTERS, 2006, 47 (52) :9173-9176

[7] Solvias Josiphos ligands: from discovery to technical applications [J].

Blaser, HU ;

Brieden, W ;

Pugin, B ;

Spindler, F ;

Studer, M ;

Togni, A .

TOPICS IN CATALYSIS, 2002, 19 (01) :3-16

[8] Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors [J].

Bournaud, C ;

Robic, D ;

Bonin, M ;

Micouin, L .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3316-3317

[9] On the use of phosphoramidite ligands in copper-catalyzed asymmetric transformations with trialkylaluminum reagents [J].

Bournaud, Chloee ;

Falciola, Caroline ;

Lecourt, Thomas ;

Rosset, Stephane ;

Alexakis, Alexandre ;

Micouin, Laurent .

ORGANIC LETTERS, 2006, 8 (16) :3581-3584

[10] Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].

Cabrera, S ;

Arrayás, RG ;

Alonso, I ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947

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