Asymmetric Synthesis of α-Hydrazino Ketones

Asymmetric α-Amination Reaction of Alkenoate Cyclic Esters Catalyzed by Chiral Tin Alkoxides: A. Yanagisawa, Y. Yamashita, C. Uchiyama, R. Nakano, M. Horiguchi, K. Ida
Synlett 2019, DOI: 10.1055/s-0037-1612278

Chiral non-racemic α-amino ketones and related analogues are important compounds in organic chemistry. α-Amination of carbonyl compounds is an attractive entry to these molecules, and the catalytic stereocontrolled version of this process continues to be actively investigated for expanding scope and optimizing performance and conditions of the reaction. The group of Professor Akira Yanagisawa from Chiba University (Japan) has now reported the use of chiral tin alkoxides to catalyze the reaction of dialkyl azodicarboxylates with alkenoate cyclic esters. 

Professor Yanagisawa said: “The use of a (R)-BINOL-derived chiral tin dialkoxide as the in situ generated chiral catalyst has enabled the synthesis of various optically active α-hydrazino ketones possessing three ester functional groups, and enantioselectivities of up to 91% ee have been realized.” 

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