PPh3-Mediated [3+2] Cycloaddition Reaction between Bis-Substituted Allenoate and N-Tosylaldimines to Construct 2-Pyrrolines

Xiangwen Kong; Lihua Liu; Siqin Luo; Shilu Fan; Haisheng Qian; Hua Xiao

doi:10.1055/s-0037-1609489

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(09): 1244-1248
DOI: 10.1055/s-0037-1609489

letter

PPh₃-Mediated [3+2] Cycloaddition Reaction between Bis-Substituted Allenoate and N-Tosylaldimines to Construct 2-Pyrrolines

Autor*innen

Xiangwen Kong

^aDepartment of Pharmaceutical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, P. R. of China eMail: xiaohual@hfut.edu.cn
Lihua Liu

^aDepartment of Pharmaceutical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, P. R. of China eMail: xiaohual@hfut.edu.cn
Siqin Luo

^aDepartment of Pharmaceutical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, P. R. of China eMail: xiaohual@hfut.edu.cn
Shilu Fan

^bDepartment of Chemistry, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, P. R. of China
Haisheng Qian

^aDepartment of Pharmaceutical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, P. R. of China eMail: xiaohual@hfut.edu.cn
Hua Xiao*

^aDepartment of Pharmaceutical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, P. R. of China eMail: xiaohual@hfut.edu.cn

Abstract

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Abstract

A triphenylphosphine-promoted [3+2] cycloaddition of α,γ-bis-substituted allenoates and N-tosylaldimines followed by alkene isomerization was disclosed, affording a series of functionalized 2-pyrroline derivatives in moderate chemical yields with random diastereoselectivities.

Key words

nucleophilic catalysis - allenoate - cycloaddition - triphenylphosphine - 2-pyrroline

Volltext

Referenzen

References and Notes

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13 Conducting the reaction at 0 °C or –10 °C resulted in a poor yield and had little influence on diastereoselectivity.
14 See the Supporting Information for details. Other imines activated by alternative electron-withdrawing groups on the nitrogen atom failed to give satisfying results: The use of N-(tert-butoxycarbonyl)benzaldimine provided an intractable and complicated mixture, and the reaction with cyclic ketimine benzo[d]isothiazole 1,1-dioxide gave a trace amount of analogous cycloaddition product.
15 CCDC 1811285 (3j) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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18 General Procedure Into a solution of N-tosyl aldimine 1 (0.1 mmol) and bis-substituted allenoate 2 (0.2 mmol) in toluene (1.0 mL) was added PPh₃ (0.06 mmol) in one portion. The resulting mixture was stirred at r.t. and monitored by TLC. After the reaction was complete, the mixture was directly subjected to flash column chromatography (PE/EtOAc = 10:1 as the eluent) to furnish the corresponding product 3. Diethyl 2-(5-Phenyl-1-tosyl-4,5-dihydro-1H-pyrrol-2-yl)succinate (3a) Light yellow liquid; 78% yield; inseparable mixture of two diastereoisomers (major and minor), d.r. = 1.2:1. ¹H NMR (600 MHz, CDCl₃): δ = 7.83 (d, J = 8.2 Hz, 2 H; minor), 7.75 (d, J = 8.4 Hz, 2 H; major), 7.33 (m, 2 H; both isomers), 7.31–7.23 (m, 5 H; both isomers), 5.17 (s 1 H; both isomers), 5.24 (s, 1 H; major), 5.11 (s, 1 H; minor), 5.10–5.05 (m, 1 H; both isomers), 4.57–4.49 (m, 1 H; both isomers), 4.27–4.10 (m, 4 H; both isomers), 3.08–3.02 (m, 1 H; both isomers), 2.82–2.74 (m, 1 H; both isomers), 2.65–2.48 (m, 1 H; both isomers), 2.45 (s, 3 H; minor), 2.42 (s, 3 H; major), 2.28–2.20 (m, 1 H; both isomers), 1.28–1.21 (m, 6 H; both isomers). ¹³C NMR (150 MHz, CDCl₃): δ = 171.8, 171.3, 171.2, 171.0, 144.1, 143.9, 142.6, 142.5, 140.8, 135.5, 134.2, 129.7, 129.6, 128.7, 128.5, 127.8, 127.7, 126.0, 125.8, 114.4, 114.3, 64.7, 64.6, 61.4, 61.2, 60.9, 60.8, 42.2, 41.5, 36.7, 36.2, 35.7, 35.6, 29.7, 21.6, 21.5, 14.1, 14.0. HRMS (ESI): m/z calcd for [M]⁺(C₂₅H₂₉NO₆S): 471.1716; found: 471.1719.

Zusatzmaterial

Supporting Information (PDF) (opens in new window)