Selective isomerization–carbonylation of a terpene trisubstituted double bond

Literature Information

Publication Date 2014-09-03
DOI 10.1039/C4GC01233J
Impact Factor 10.182
Authors

Hanna Busch, Florian Stempfle, Sandra Heß, Etienne Grau, Stefan Mecking


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Abstract

Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization–functionalization approach. Alkoxycarbonylation with [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)2] as a catalyst precursor occurs with >97% selectivity for the terminal diester dimethyl-3,7-dimethylnonane-dioate. This prevails much over the typical cationic methoxyaddition. The reactive primary carboxy group formed allows for e.g. the preparation of the high molecular weight novel polyester poly[3,7-dimethylnonanediyl-3,7-dimethylnonanedioate].

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