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. 2017 Aug 4;82(15):8304-8308.
doi: 10.1021/acs.joc.7b01381. Epub 2017 Jul 19.

Direct Catalytic Asymmetric Aldol Addition of an α-CF3 Amide to Arylglyoxal Hydrates

Akinobu Matsuzawa  1 , Hidetoshi Noda  1 , Naoya Kumagai  1 , Masakatsu Shibasaki  1
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Direct Catalytic Asymmetric Aldol Addition of an α-CF3 Amide to Arylglyoxal Hydrates

Akinobu Matsuzawa et al. J Org Chem. .

Abstract

Direct asymmetric aldol addition of an α-CF3 amide to arylglyoxal hydrates was promoted by a chiral catalyst comprising a soft Lewis acidic Cu(I), a chiral bisphosphine ligand, and DBU. The 7-azaindoline moiety of the amide facilitates its enolization and stabilizes the thus-generated Cu enolate, furnishing enantioenriched aldol adducts.

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