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Communication | Special issue | Vol 99, No. 2, 2019, pp.841-847
Published online, 8th February, 2019
DOI: 10.3987/COM-18-S(F)77
Tripeptide-Catalyzed Asymmetric Aldol Reaction of Trifluoromethylated Aromatic Ketones with Acetone

Kazumasa Kon, Yoshihito Kohari,* and Miki Murata

*School of Earth, Energy and Environmental Engineering, Faculty of Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan

Abstract

The development of H-Pro-Gly-Ala-OH (3d) to realize an inexpensive and simple organocatalytic system for the direct asymmetric aldol reaction of trifluoromethylated aromatic ketone 1 with acetone was achieved. The 3d-catalyzed aldol reaction of 1a1j provided various aldol adducts 4a4j with up to 81% yield and 77% ee. An investigation of the transition state via DFT calculations revealed that hydrogen bonding was important for the revelation of the enantioselectivity.