1219152-65-4Relevant academic research and scientific papers
Synthesis of α,β-diamino acid derivatives via asymmetric Mannich reactions of glycine imino esters catalyzed by a chiral phosphoramidite·silver complex Dedicated to the memory of Prof. Ekkehard Winterfeldt
Cayuelas, Alberto,Serrano, Loane,Njera, Carmen,Sansano, Jos M.
, p. 1647 - 1653 (2015/03/03)
AgOTf·phosphoramidite complexes efficiently catalyze the enantioselective Mannich-type reaction between benzophenone-imine glycine methyl ester and N-tosyl aldimines in the absence of a base. The corresponding syn-adducts, which are the direct precursors of α,β-diamino acids, are obtained with moderate to good syn-diastereoselectivities (up to 9:1) and high enantioselectivities (up to 99% ee).
Substrate-controlled diastereoselectivity switch in catalytic asymmetric direct mannich reaction of glycine derivatives with imines: from anti- to syn-α,β-diamino acids
Hernandez-Toribio, Jorge,Array, Ramon Gomez,Carretero, Juan Carlos
supporting information; experimental part, p. 1153 - 1157 (2010/05/19)
(Chemical equation Presented) Back and forth: A diastereoselectivity switch has been devised in the Fesulphos-CuI-catalyzed glycine direct Mannich reaction with N-(8-quinolyl)sulfonyl imines by tuning the steric and electronic properties of the glycine component (see scheme). αβ-Diamino acids of syn configuration are produced under high diastereo- and enantiocontrol with glycinate esters derived from electron-deficient benzophenonetype ketimines, in contrast to aldiminederived pronucleophiles that lead to anti-configured products.
