Asymmetric Conjugate Addition of Ketones to Maleimides Using Diaminomethyleneindenedione Organocatalyst

Kosuke Nakashima; Masahiro Kawada; Shin-ichi Hirashima; Mana Kato; Yuji Koseki; Tsuyoshi Miura

doi:10.1055/s-0034-1380382

Synlett, Table of Contents

Synlett 2015; 26(09): 1248-1252
DOI: 10.1055/s-0034-1380382

letter

Asymmetric Conjugate Addition of Ketones to Maleimides Using Diaminomethyleneindenedione Organocatalyst

Kosuke Nakashima

Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Email: tmiura@toyaku.ac.jp

,

Masahiro Kawada

Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Email: tmiura@toyaku.ac.jp

,

Shin-ichi Hirashima

Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Email: tmiura@toyaku.ac.jp

,

Mana Kato

Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Email: tmiura@toyaku.ac.jp

,

Yuji Koseki

Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Email: tmiura@toyaku.ac.jp

,

Tsuyoshi Miura*

Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan Email: tmiura@toyaku.ac.jp

› Author Affiliations

Abstract

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Abstract

A novel diaminomethyleneindenedione (DMI) organocatalyst efficiently promotes the asymmetric conjugate addition of a ketone to a maleimide to afford the corresponding addition product in a high yield with up to 99% enantiomeric excess.

Key words

organocatalyst - maleimide - conjugate addition - asymmetric reaction - ketone

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References

References and Notes
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13 Organocatalyst 3 Yellow powder; mp 179–180 °C; [α]_D ²⁹ –10.9 (c 1.00, CH₂Cl₂). ¹H NMR (400 MHz, CDCl₃): δ = 9.61 (br s, 1 H), 9.02 (d, J = 9.8 Hz, 1 H), 7.87 (s, 3 H), 7.61–7.57 (m, 2 H), 7.53–7.49 (m, 2 H), 5.13 (dd, J = 6.0, 16.3 Hz, 1 H) 4.88 (dd, J = 6.5, 16.3 Hz, 1 H), 3.15–3.06 (m, 1 H), 2.82–2.76 (m, 1 H), 1.89–0.87 (m, 10 H). ¹³C NMR (100 MHz, CDCl₃): δ = 192.4, 161.5, 140.3, 138.6, 132.4 (q, ² J _C–F = 33.7 Hz), 132.3, 127.1, 123.1 (q, ¹ J _C–F = 273 Hz), 121.9, 120.5, 93.7, 61.3, 55.7, 47.7, 34.1, 33.2, 24.8, 24.2. Anal. Calcd for C₂₅H₂₃F₆N₃O₂: C, 58.71; H, 4.53; N, 8.22. Found: C, 58.62; H, 4.52; N, 8.22.
14 Typical Procedure of the Conjugate Additions to Maleimides Using 3 To a mixture of N-phenylmaleimide (4a, 34.6 mg, 0.200 mmol) and acetone (73.4 μL, 1.00 mmol) in p-xylene (0.4 mL) was added organocatalyst 3 (20.5 mg, 0.040 mmol) and benzoic acid (2.5 mg, 0.020 mmol) at r.t. After stirring in closed tube at 40 °C for 48 h, the reaction mixture was directly purified by flash column chromatography on silica gel with a 3:2 to 1:1 mixture of hexane and EtOAc to afford 5a (37.3 mg, 81%) as a white powder.

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