Direct Mannich Reaction of Glycinate Schiff Bases with N-(8-Quinolyl)sulfonyl Imines: A Catalytic Asymmetric Approach to anti-alpha,beta-Diamino Esters

作者：Hernandez Toribio Jorge; Gomez Arrayas Ramon; Carretero Juan C

来源：Journal of the American Chemical Society, 2008, 130(48): 16150-+.

DOI：10.1021/ja807583n

An efficient catalytic enantioselective direct Mannich reaction of glycinate Schiff bases with aryl imines leading to anticonfigured orthogonally protected alpha,beta-diaminoesters has been realized. Keys to success in this new catalyst system are the use of Fesulphos/Cu(CH(3)CN)(4)PF(6) (3-5 mol%) as a Lewis acid catalyst and readily available N-(8-quinolyl)sulfonyl-protected aldimines as substrates, affording excellent levels of diastereo- (typically anti/syn >90:10) and enantiocontrol (typically >= 90% ee). A remarkable feature of this catalyst system is that it allows the construction of products with a tetrasubstituted carbon stereocenter at C-alpha in a highly diastereo- and enantiocontrolled manner.

• 出版日期2008-12-3