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Abstract

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Communication | Regular issue | Vol 94, No. 3, 2017, pp. 441 - 447
Published online: 17th March, 2017
DOI: 10.3987/COM-16-13642
Stereoselective Aza-Henry Reaction of 3-Nitro-dihydro-2(1H)-quinolones with N-Boc-Aldimines under the Catalysis of Chiral Ammonium Betaines

Daisuke Uraguchi, Masahiro Torii, Kohsuke Kato, and Takashi Ooi*

*Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan

Abstract

A highly enantioselective aza-Henry reaction between 3-nitro-dihydro-2(1H)-quinolones and N-Boc-aldimines was developed by using a chiral ammonium betaine as a catalyst. This protocol provides a direct synthetic method for accessing hydroquinoline derivatives possessing a tetrasubstituted stereogenic center at the C3 position and casts light on the utility of the α-functionalization of dihydroquinolones.

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