- Stereoselective Synthesis of 2Z,4E-Dienals by Addition of Organometallic Reagents to Pyrylium Perchlorate
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A facile and stereoselective approach to 2Z,4E-dienals and derived products is presented.The method involves addition of an organometallic reagent to a pyrylium salt, followed by electrocyclic ring-opening of the intermediate 2H-pyran, to give the desired Z,E-dienal, usually with greater than 95percent stereochemical purity.These dienals may be trapped in situ with a second organometallic reagent, or oxidised or redused, without loss of stereochemical integrity.The synthesis of (1,3Z,5E)-undeca-1,3,5-triene, a component of the essential oils of the brown Hawaiian seaweeds Dictyopteris plagiogramma and D. australis, is reported to illustrate the simplicity of the procedure.
- Furber, Mark,Herbert, John M.,Taylor, Richard J. K.
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p. 683 - 690
(2007/10/02)
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