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Full Paper
Development of Dirhodium(II)-Catalyzed Generation and Enantioselective 1,3-Dipolar Cycloaddition of Carbonyl Ylides
Article first published online: 5 OCT 2001
DOI: 10.1002/1521-3765(20011015)7:20<4465::AID-CHEM4465>3.0.CO;2-W
© 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
7:20<>1.0.CO;2-T/asset/cover.gif?v=1&s=6ddf18a42b837d740ae5f0078f22599a8ece240f "Chemistry - A European Journal")
Additional Information
How to Cite
Hodgson, D. M., Stupple, P. A., Pierard, F. Y. T. M., Labande, A. H. and Johnstone, C. (2001), Development of Dirhodium(II)-Catalyzed Generation and Enantioselective 1,3-Dipolar Cycloaddition of Carbonyl Ylides. Chemistry - A European Journal, 7: 4465–4476. doi: 10.1002/1521-3765(20011015)7:20<4465::AID-CHEM4465>3.0.CO;2-W
Publication History
- Issue published online: 5 OCT 2001
- Article first published online: 5 OCT 2001
- Manuscript Received: 18 JUN 2001
Keywords:
- asymmetric catalysis;
- catalysts;
- cycloaddition;
- diazo compounds;
- rhodium
Graphical Abstract
7:20<4465::AID-CHEM4465>3.0.CO;2-W/asset/image_m/mcontent.gif?v=1&s=a68f31a20d11623418cbefb70eb014013d5203ec "Thumbnail image of graphical abstract")
Ask more of your catalyst! Herein is described the evolution of chiral rhodium catalysts that not only are able to form carbonyl ylides from diazo substrates, but are also capable of remaining associated with the ylide to effect efficient asymmetric cycloaddition (see scheme).
Abstract
Catalytic, enantioselective, tandem carbonyl ylide formation/cycloaddition of 2-diazo-3,6-diketoester 2 with the use of dirhodium tetrakiscarboxylate and tetrakisbinaphtholphosphate catalysts to give the cycloadducts 3 in good yields and up to 90 % ee is described.