Dalton Transactions (Print Edition) 2013-01-07

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

Index: Dalton Trans. 42(1) , 292-8, (2013)

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Abstract

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.

Related Compounds

  • Diethyl malonate
  • nitromethane
  • Ethyl acetoacetate

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