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Molecules 2006, 11(2), 177-196; doi:10.3390/11020177
Article

Synthesis of New Chiral Amines with a Cyclic 1,2-Diacetal Skeleton Derived from (2R, 3R)-(+)-Tartaric Acid

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Received: 27 January 2006 / Revised: 15 March 2006 / Accepted: 16 March 2006 / Published: 17 March 2006
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Abstract

The syntheses of new chiral cyclic 1,2-diacetals from (2R, 3R)-( )-tartaric acidare described. C2-symmetrical diamines were prepared via direct amidation of the tartrate orfrom the corresponding bismesylate via reaction with sodium azide. For C1-symmetricalcompounds, the Appel reaction was used to form the key intermediate, amonochlorocarbinol, from the diol. Some of the new chiral compounds, produced in good tohigh yields, may be potentially useful as asymmetric organocatalysts or as nitrogen andsulfur chelating ligands for asymmetric metal catalyzed reactions. Thus, a bis-N-methyl-methanamine derivative, used in substoichiometric amounts, was found to catalyze theenantioselective addition of cyclohexanone to (E)-β-nitrostyrene with highdiastereoselectivity (syn / anti = 92:8), albeit giving moderate optical purity (syn: 30 %).
Keywords: Chiral amines; 1; 2-diacetals; organocatalysts; asymmetric Michael additions; chiral ligands Chiral amines; 1; 2-diacetals; organocatalysts; asymmetric Michael additions; chiral ligands
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Barros, M.T.; Phillips, A.M.F. Synthesis of New Chiral Amines with a Cyclic 1,2-Diacetal Skeleton Derived from (2R, 3R)-(+)-Tartaric Acid. Molecules 2006, 11, 177-196.

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