1219152-49-4Relevant articles and documents
Cyclopropenimine-catalyzed enantioselective mannich reactions of tert -butyl glycinates with N -Boc-imines
Bandar, Jeffrey S.,Lambert, Tristan H.
supporting information, p. 11799 - 11802 (2013/09/02)
Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines are effective substrates for this transformation. A preparative-scale reaction to deliver >90 mmol of product is shown using 1 mol % catalyst. The products of this transformation can be converted into several useful derivatives.
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.