Synlett 2014; 25(19): 2733-2737
DOI: 10.1055/s-0034-1378649
cluster
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Construction of Azabicyclo[2.2.1]heptanes Bearing Two Quaternary Stereogenic Centers via Silver(I)-Catalyzed 1,3-Dipolar Cyclo­addition of Cyclic Azomethine Ylides

Zhi-Yong Xue
a  College of Chemistry and Chemical Engineering, Wuhan Textile University, Wuhan 430073, P. R. of China
b  College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China   Fax: +86(27)68754067   Email: cjwang@whu.edu.cn
,
Yong Xiong
b  College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China   Fax: +86(27)68754067   Email: cjwang@whu.edu.cn
,
Chun-Jiang Wang*
b  College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China   Fax: +86(27)68754067   Email: cjwang@whu.edu.cn
c  State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 23 June 2014

Accepted after revision: 19 July 2014

Publication Date:
25 August 2014 (online)


Abstract

Ag(I)/TF-BiphamPhos-catalyzed asymmetric 1,3-dipolar cycloaddition reaction of cyclic azomethine ylides with N-substituted maleimides has been developed for the efficient construction of azabicyclo[2.2.1]heptanes, a valuable structural motif for drug discovery, in good yields with high diastereoselectivities (up to 16:1 dr) and excellent enantioselectivities (up to 97% ee). The key feature of the present methodology is that two quaternary stereogenic centers were constructed efficiently among the generated four contiguous stereocenters in the annulation process.

Supporting Information

 
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  • 16 Typical Experimental Procedure for the Synthesis of (3aS,4R,7R,7aR)-Methyl 1,3-Dioxo-2,7-diphenyloctahydro-1H-4,7-epiminoisoindole-4-carboxylate (3a): Under an argon atmosphere (S)-TF-BiphamPhos L2 (6.0 mg, 0.0075 mmol) and AgOAc (1.2 mg, 0.007 mmol) were dissolved in CH2Cl2 (2 mL), and stirred at r.t. for about 1 h. Then, the cyclic imino ester 1a (0.23 mmol), K2CO3 (0.04 mmol) and N-substituted maleimides 2a (0.35 mmol) were added sequentially. Once starting material was consumed (monitored by TLC), the mixture was filtered through celite and the filtrate was concentrated to dryness. The crude product was analyzed by 1H NMR to determine the exo/endo ratio (16:1). Column chromatographic purification of the crude mass on silica gel (EtOAc–petroleum ether, 1:3) gave 3a (80% yield) as a white solid, which was then directly analyzed by chiral HPLC to determine the enantiomeric excess. Compounds 3am were prepared by following a similar procedure. Data for 3a: [α]25 D –53.5 (c = 1.0, CHCl3). 1H NMR (300 MHz, CDCl3, TMS): δ = 7.31–7.47 (m, 8 H), 7.19–7.22 (m, 2 H), 3.89 (s, 3 H), 3.43 (d, J = 6.9 Hz, 1 H), 3.17 (d, J = 6.9 Hz, 1 H), 2.40–2.49 (m, 1 H), 2.24–2.32 (m, 1 H), 2.04–2.13 (m, 1 H), 1.90–1.98 (m, 1 H). 13C NMR (75 MHz, CDCl3, TMS): δ = 35.25, 38.42, 52.32, 52.45, 53.23, 70.62, 72.29, 126.10, 127.82, 128.28, 128.86, 131.67, 137.92, 170.80, 173.58, 174.66. The enantioselectivity (97% ee) was determined by HPLC (Chiralcel AS-H; i-PrOH–hexane, 30:70; flow rate: 1.0 mL/min, λ = 220 nm); t R = 12.55 and 16.89 min. HRMS: m/z calcd [M + H+] for [C22H20N2O4 + H+]: 377.1501; found: 377.1493.
  • 17 Co-crystal data for (3aS,4R,7R,7aR)-3b and CH2Cl2 (1:1): C23H21Cl3N2O4, M r = 495.77, T = 296 K, monoclinic, space group P2(1), a = 10.3864(14), b = 9.6576(13), c = 11.8090(16) Å, V = 1179.8(3) Å3, Z = 2, 7791 reflections measured, 4747 unique (R int = 0.0632) which were used in all calculations. The final wR 2 = 0.1674 (all data), Flack χ = 0.07(11). CCDC 977862 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].