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Synlett 2018; 29(15): 2006-2010
DOI: 10.1055/s-0037-1610232
letter
© Georg Thieme Verlag Stuttgart · New York

Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides

Tianyun Zhou
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
b   Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China
,
Jigang Gao
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Guofeng Liu
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Xukai Guan
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Dong An
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
,
Suoqin Zhang*
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
b   Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, College of Life Sciences, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China
,
Guangliang Zhang*
a   College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. of China   Email: zhgl_jl@jlu.edu.cn   Email: suoqin@jlu.edu.cn
› Author Affiliations
We are grateful for financial support from the National Natural ­Science Foundation of China (Nos. 21372098 and 20802025) and the Jilin Province Science & Technology Development Program (Nos. 20150203006GX and 20140307004GX).
Further Information

Publication History

Received: 01 March 2018

Accepted after revision: 13 July 2018

Publication Date:
23 August 2018 (online)

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Abstract

Chiral butenolides were synthesized by the enantioselective vinylogous Mannich reaction. Chiral (VAPOL)-type imidodiphosphoric acids are efficient catalysts for the asymmetric vinylogous Mannich (AVM) reaction of aldimines and trimethylsiloxyfuran in toluene. Under the optimized conditions, a series of butenolides were obtained with high yields (up to 98%) and enantioselectivities (up to 97% ee) as well as excellent diastereoselectivities (up to 99:1 dr).

Key words

butenolides - trimethylsiloxyfuran - organocatalysis - enantio­selectivity - asymmetric vinylogous Mannich reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610232.
  • Supporting Information
 

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  • 18 General Procedure for the Asymmetric Vinylogous Mannich Reaction of Aldimines with 2-(Trimethylsilyloxy)furan A mixture of aldimine 6 (0.1 mmol), VAPOL imidodiphosphoric acid 4 (5 mol%) HP-β-CD (4 mg), toluene (1 mL) was stirred at –40 °C for 15 min. Then, 2-(trimethylsilyloxy)furan 7 (0.3 mmol) was added under an argon atmosphere at –40 °C. After the reaction was completed (monitored by TLC), the mixture was purified by silica gel chromatography (ethyl ­acetate/petroleum ether 1:6) to directly afford product 8. (S)-5-[(R)-Phenyl(phenylamino)methyl]furan-2(5H)-one (8a) Colorless oil, 97% yield, [α]D 20 = –124.2 (c = 1.5, CHCl3), 80% ee, 93:7 dr [DaicelChiralcel OJ-H column, n-hexane/ethanol 80:20, 1.0 mL/min, λ = 254 nm, t(major) = 27.865 min, t(minor) = 32.746 min]. 1H NMR (400 MHz, DMSO-d 6): δ = 7.81 (d, J = 8.0 Hz, 1 H),7.43 (d, J = 4.0 Hz, 2 H), 7.30 (t, J = 8.0 Hz, 2 H), 7.24–7.21 (m, 1 H), 7.02 (t, J = 8.0 Hz, 2 H), 6.68 (d, J = 8.0 Hz, 2 H), 6.53 (t, J = 8.0 Hz, 1 H), 6.40 (d, J = 8.0 Hz, 1 H), 6.17–6.15 (m, 1 H), 5.50 (d, J = 4.0 Hz, 1 H), 4.90–4.87 (m, 1 H) ppm. 13C NMR (100 MHz, DMSO-d 6): δ = 173.1, 156.5, 147.7, 138.8, 129.2, 128.4, 128.3, 127.9, 122.2, 117.0, 113.7, 85.5, 58.6 ppm. HRMS (ESI): m/z [M + H]+ calcd for C17H15NO2: 266.1103; found: 266.1188.