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Synlett 2009(17): 2831-2835  
DOI: 10.1055/s-0029-1217968
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Homocoupling of (1-Acyloxyvinyl)silanes: Synthesis of 1,3-Diene-2,3-diyl Diesters and Their Derivatives

Yanni Yue, Hiroki Yamamoto, Motoki Yamane*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanynag Link, Singapore 637371, Singapore
Fax: +6567911961; e-Mail: yamane@ntu.edu.sg;
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Publikationsverlauf

Received 29 June 2009
Publikationsdatum:
09. September 2009 (online)

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Abstract

1,3-Diene-2,3-diyl diesters are synthesized by rhodium-catalyzed homocoupling of (1-acyloxyvinyl)silanes. Double transmetalation between vinylsilane and rhodium intermediate in a single catalytic cycle is the key in this reaction. From the homocoupling products, symmetrical α-diketone and its monoacetal are easily synthesized.

Key words

homocoupling - rhodium catalyst - organosilicon compounds - vinyl ester - conjugated diene

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1

Current address: Department of Chemistry, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8551, Japan.

16

CCDC 737226 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.