Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding α-methylamino acid products.

Stephanie Oerum, Peter Krabbe, Magnus Schau-Magnussen, Søren Furbo, Jesper Bendix, Anders Hammershøi

Department of Chemistry, University of Copenhagen, DK-2100 Copenhagen Ø, Denmark.

Dalton transactions (Cambridge, England : 2003) 2013 Jan 7

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Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L(4)Co(O(2)CCH=NCH(3))](2+) [L(4) = (en)(2) (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-R(C)*-S(N)*)-[Co(en)(2)(O(2)CCH[CH(2)NO(2)]NHCH(3))]ZnCl(4) and rac-(Δ*-R(C)*-S(N)*)-[Co(en)(2)(O(2)CCH[CH(2)COCH(3)]NHCH(3))]ZnCl(4), were established by X-ray diffraction.

Citation

Stephanie Oerum, Peter Krabbe, Magnus Schau-Magnussen, Søren Furbo, Jesper Bendix, Anders Hammershøi. Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding α-methylamino acid products. Dalton transactions (Cambridge, England : 2003). 2013 Jan 7;42(1):292-8