120254-80-0Relevant articles and documents
Regiodivergent cyclobutanone cleavage: Switching selectivity with different Lewis acids
Souillart, Laetitia,Cramer, Nicolai
, p. 1863 - 1867 (2015)
The exploitation of strain release in small rings as driving force to enable complex transformations is a powerful synthetic tool. Among them, cyclobutanones are particularly versatile substrates that can be elaborated in a wide variety of structurally diverse building blocks. Herein, Lewis acid catalyzed rearrangement reactions are presented that provide selective access to two structurally distinct polycyclic scaffolds, that is, indenylacetic acid derivatives and benzoxabicyclo[3.2.1]octan-3-ones. The choice of the Lewis acid fully controls the reaction pathway and the regioselectivity of the cyclobutanone C-C bond cleavage site.
Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts
Mao, Hui,Kim, Dong Wan,Shin, Hun Yi,Song, Choong Eui,Yang, Jung Woon
supporting information, p. 1355 - 1362 (2017/02/15)
The regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives was achieved through transition-metal-free, reductive cyclisation of ortho-formyl trans-cinnamaldehydes with Hantzsch ester in the presence of an aminocatalyst. In particular, cycloolefin isomerisation of the resulting products could be inhibited efficiently by the introduction of a sterically demanding stereo-defined aminocatalyst.
Highly enantioselective rhodium(I)-catalyzed carbonyl carboacylations initiated by C-C bond activation
Souillart, Laetitia,Cramer, Nicolai
supporting information, p. 9640 - 9644 (2014/11/27)
The lactone motif is ubiquitous in natural products and pharmaceuticals. The Tishchenko disproportionation of two aldehydes, a carbonyl hydroacylation, is an efficient and atom-economic access to lactones. However, these reaction types are limited to the transfer of a hydride to the accepting carbonyl group. The transfer of alkyl groups enabling the formation of C-C bonds during the ester formation would be of significant interest. Reported herein is such asymmetric carbonyl carboacylation of aldehydes and ketones, thus affording complex bicyclic lactones in excellent enantioselectivities. The rhodium(I)-catalyzed transformation is induced by an enantiotopic C-C bond activation of a cyclobutanone and the formed rhodacyclic intermediate reacts with aldehyde or ketone groups to give highly functionalized lactones. Delivering the goods: Asymmetric carbonyl carboacylations of aldehydes and ketones provide access to functionalized bicyclic lactones. The rhodium(I)-catalyzed transformation is induced by an enantiotopic C-C bond activation of a cyclobutanone and the transient rhodacyclic adds across an appended carbonyl group to deliver the lactones in excellent enantioselectivities.
