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EnglishFunctionalized allyl halides, useful starting materials for the prepn. of substituted organometallic reagents can be simply obtained by a straightforward approach. Hoveyda's ruthenium carbene catalyst, used in catalytic amt. (2 mol%), is able to promote the cross metathesis of allyl bromide and chloride with a variety of different substituted olefins giving the corresponding functionalized allyl halides in satisfactory yields. Trans-Olefins are obtained as major diastereoisomers reaching 90:10 (trans:cis) ratio when allyl chloride is used as the metathesis partner. This reaction represents a simple and accessible way for the prepn. of valuable precursors for functionalized organometallic reagents. In particular, the use of functionalized allyl bromides in the enantioselective Nozaki-Hiyama reaction promoted by [Cr(Salen)Cl] is presented.
| Titolo: | A Cross Metathesis Based Protocol for the Effective Synthesis of Functionalised Allyl Bromides and Chlorides |
| Autore/i: | BANDINI, MARCO; COZZI, PIER GIORGIO; MELCHIORRE, PAOLO; LICCIULLI, SEBASTIANO; UMANI RONCHI, ACHILLE |
| Autore/i Unibo: | |
| Anno: | 2004 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1055/s-2004-815936 |
| Abstract: | Functionalized allyl halides, useful starting materials for the prepn. of substituted organometallic reagents can be simply obtained by a straightforward approach. Hoveyda's ruthenium carbene catalyst, used in catalytic amt. (2 mol%), is able to promote the cross metathesis of allyl bromide and chloride with a variety of different substituted olefins giving the corresponding functionalized allyl halides in satisfactory yields. Trans-Olefins are obtained as major diastereoisomers reaching 90:10 (trans:cis) ratio when allyl chloride is used as the metathesis partner. This reaction represents a simple and accessible way for the prepn. of valuable precursors for functionalized organometallic reagents. In particular, the use of functionalized allyl bromides in the enantioselective Nozaki-Hiyama reaction promoted by [Cr(Salen)Cl] is presented. |
| Data prodotto definitivo in UGOV: | 2005-10-18 15:02:46 |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/7981
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