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Synfacts 2006(12): 1262-1262  
DOI: 10.1055/s-2006-949501
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Hydroformylation of Internal Alkenes by Encapsulated Rhodium

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Kuil, T. Soltner, P. W. N. M. van Leeuwen, J. N. H. Reek*
University of Amsterdam, The Netherlands
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Publikationsdatum:
22. November 2006 (online)

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Significance

This is an outstanding report with unprecedented regioselectivity for hydroformylation of internal alkenes. The use of encapsulated rhodium gives extremely high regioselectivity, whereas a standard rhodium catalyst (not encapsulated) gives nearly a 1:1 mixture of isomers. When the reaction is performed at 25 °C, the highest regio­selectivity is obtained, and the selectivity decreases with an increase in temperature due to isomerization pathways capable at the elevated temperatures.