cyclohexane derivativescyclohexane derivatives Q 0040
-094Intramolecular Competitive Ireland Claisen Rearrangements: Stereoselective Synthesis of Alkylidene Cyclohexenes.-The Ireland Claisen rearrangement of in situ generated bis-allyl ketene acetals is investigated. Thus, treatment of the esters (I) with triisopropylsilyl triflate affords an E/Z-mixture of alkylidene cyclohexenes (II) and (III) after desilylation. Introduction of a substituent on the endo double bond results in reversal of the stereoselectivity providing the E-diene (V) exclusively. Furthermore, rearrangement of the (R)-carvone-derived substrate (VI) yields the E-diene (VII) with satisfying chirality transfer by 1,6-asymmetric induction.-(ZHANG, X.; MCINTOSH, M. A.; Tetrahedron Lett. 39 (1998) 39, 7043-7046; Dep. Chem.
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