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Synlett 2018; 29(15): 2006-2010
DOI: 10.1055/s-0037-1610232
DOI: 10.1055/s-0037-1610232
letter
Chiral VAPOL Imidodiphosphoric Acid-Catalyzed Asymmetric Vinylogous Mannich Reaction for the Synthesis of Butenolides
Authors
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)
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 reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610232.
- Supporting Information (PDF)
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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.
For chiral phosphoric acids and their derivatives, see:
For chiral imidodiphosphoric acids, see: