Synfacts 2007(10): 1102-1102  
DOI: 10.1055/s-2007-969004
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Axially Chiral Dicarboxylic Acid Catalyzed Asymmetric Mannich Reaction

Contributor(s): Benjamin List, Subhas Chandra Pan
T. Hashimoto, K. Maruoka*
Kyoto University, Japan
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Publikationsverlauf

Publikationsdatum:
07. November 2007 (online)

Significance

The authors have introduced novel axially chiral dicarboxylic acids for an asymmetric Mannich reaction of N-Boc imines and diazo compounds. After evaluating different substituents at the 3,3′-position of the binaphthyl moiety, catalyst 1 has been found to give high enanatioselectivities. With 5 mol% of catalyst 1, moderate to high yields (53-89%) and excellent enantioselectivities (er = 92:8 to 98:2) have been obtained for different arylaldehyde-derived N-Boc imines and tert-butyl ­diazoacetate. Dimethyl diazomethylphosphonate has also been used as the nucleophile and excellent enantioselectivities (er = 96:4 to 98:2) have been obtained.