Annulation with Methyl 4-(Triphenylphosphoranylidene) acetoacetate. Application to the Synthesis of a 1,3-Benzenedicarboxylate Derivative

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• The 1H, 13C and 19F nmr of the mixture of 3a and 3b indicated a single stereoisomer of each compound. The relative stereo-chemistry of the isobutyl and the methoxycarbonyl groups in 3b was tentatively assigned to be trans based upon the fact that the cyclohexyl ring proton adjacent to the methoxycarbonyl group displayed a sharp singlet at 3.28 ppm in the 1H nmr spectrum. The lack of coupling with the adjacent ring proton is consistent with a dihedral angle of approximately 90° as deduced from a molecular model of the trans isomer. The stereochemistry of 3a could not be assigned unambiguously
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• Compound 2 was approximately ten-fold less active than 1 as a herbicide. A detailed comparison of biological activities will be published separately
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