24434-19-3Relevant academic research and scientific papers
Regio- and stereoselective double addition of anionic C-nucleophiles to cobalt-stabilized acetylenedicarbaldehyde
Sui-Seng, Christine,Soleilhavoup, Michele,Maurette, Luc,Tedeschi, Christine,Donnadieu, Bruno,Chauvin, Remi
, p. 1641 - 1651 (2003)
Though intrinsically unstable, Gorgues' acetylenedicarbaldehyde is an appealing, highly functional C4 synthon, which can be stabilized by η2 complexation to a Co2(CO)6 unit. In contrast to the homologous dibenzoylacetylene complex, it can be used as a normal, doubly electrophilic, non-conjugated γ-dicarbonyl substrate toward alkyl-, aryl-, and alkynyllithium compounds or magnesium bromides; these anionic C-nucleophiles do not predominantly attack at the metal-carbonyl center. The 1,4-dialkyl- and 1,4-diphenylbut2-yne-1,4-diol products are obtained with significant meso/ dl diastereoselectivity (4-66% de), which can be explained by a simple model based on X-ray diffraction data and MM calculations. The alkyl- and arylmagnesium bromide reactants are more selective than their lithium counterparts. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
