Influence of the Diene in the Hetero-Diels-Alder Reaction Catalyzed by Dirhodium(II) Carboxamidates

Abstract

Chiral dirhodium(II) carboxamidates catalyze highly stereoselective hetero-Diels-Alder reactions of aromatic aldehydes with methyl-substituted Danishefsky's dienes with high turnover numbers. The methyl substituents of the diene influence both enantioselectivity in product formation and the rate of the reaction in the presence of chiral dirhodium(II) Lewis acids.

Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity

“…Chiral dirhodium(II) complexes are currently renowned as catalysts that can effectively drive a broad spectrum of reactions with superior levels of chemo-, regio-and stereo-selectivity [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Their remarkable selectivity has reached a stage where they can function as powerful tools in building up value added molecules with complex structures [7,[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34].…”

On the Structure of Chiral Dirhodium(II) Carboxylate Catalysts: Stereoselectivity Relevance and Insights

“…This immense interest originates from their exceptional ability to effectively catalyze a broad spectrum of reactions with high levels of chemo-, regio-and stereo-selectivity. These transformations involve aziridinations [16][17][18], C-H insertions [7,19,20], ylide transformations [21][22][23][24][25], Lewis acid-promoted reactions [21,[26][27][28][29][30], cross-coupling reactions [31], cyclopropanation and cyclopropenation reactions [32][33][34][35]. In fact, they have proven their potential, particularly, in the field of asymmetric synthesis.…”

Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity

“…Their remarkable selectivity has reached a stage where they can function as a powerful tool in building up value added molecules with complex structures [7,[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34].…”