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Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Journal of the American Chemical Society (2013-08-03)
Jeffrey S Bandar, Tristan H Lambert
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(S)-2-(2,3-Bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride, ≥95%

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