Copper Hydride Catalyzed Reductive Aldol Addition/Lactonization Domino Reactions of α,β-Unsaturated Diesters

Zengchang Li; Zhenlei Zhang; Lu Yuan; Lan Jiang; Zhansheng Li; Zhengning Li

doi:10.1055/s-0033-1340673

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(5): 724-728
DOI: 10.1055/s-0033-1340673

letter

Copper Hydride Catalyzed Reductive Aldol Addition/Lactonization Domino Reactions of α,β-Unsaturated Diesters

Authors

Zengchang Li

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 eMail: znli@dl.cn
Zhenlei Zhang

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 eMail: znli@dl.cn
Lu Yuan

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 eMail: znli@dl.cn
Lan Jiang

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 eMail: znli@dl.cn
Zhansheng Li

^bCollege of Chemical Engineering, Dalian University of Technology, Dalian 116023, P. R. of China
Zhengning Li*

^aCollege of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 eMail: znli@dl.cn

Abstract

Alle Artikel dieser Rubrik

Abstract

The first copper-catalyzed reductive aldol addition/lactonization domino reactions of α,β-unsaturated dicarboxylate esters with ketones were achieved in high yields. The method, which involves easily available reagents, a flexible combination of reactants, and mild conditions, provides a simple route to functionalized lactones bearing an ester group.

Key words

reductions - aldol reactions - lactones - domino reactions - copper - catalysis

Volltext

Referenzen

References and Notes
1 Chiu P. Synthesis 2004; 2210
2 Deutsch C, Lipshutz BH, Krause N. Angew. Chem. Int. Ed. Engl. 2007; 46: 1650
3 Deutsch C, Krause N, Lipshutz BH. Chem. Rev. 2008; 108: 2916
4 Li Z, Liu G, Chiu P. Huaxue Jinzhan 2008; 20: 1909 ; Chem. Abstr. 2009, 151, 100615
5 Mahoney WS, Brestensky DM, Stryker JM. J. Am. Chem. Soc. 1988; 110: 291
6 Brestensky DM, Stryker JM. Tetrahedron Lett. 1989; 30: 5677
7 Koenig TM, Daeuble JF, Brestensky DM, Stryker JM. Tetrahedron Lett. 1990; 31: 3237
8 Kamenecka TM, Overman LE, Ly Sakata SK. Org. Lett. 2002; 4: 79
9 Chiu P, Chen B, Cheng KF. Tetrahedron Lett. 1998; 39: 9229
10 Chiu P, Szeto CP, Geng Z, Cheng K.-F. Org. Lett. 2001; 3: 1901
11 Baker BA, Bošković ZV, Lipshutz BH. Org. Lett. 2008; 10: 289
12 Welle A, Cirriez V, Riant O. Tetrahedron 2012; 68: 3435
13 Li N, Ou J, Miesch M, Chiu P. Org. Biomol. Chem. 2011; 9: 6143
14 Ou J, Wong W.-T, Chiu P. Org. Biomol. Chem. 2012; 10: 5971
15 Ou J, Wong W.-T, Chiu P. Tetrahedron 2012; 68: 3450
16 Lam HW, Joensuu PM. Org. Lett. 2005; 7: 4225
17 Zhao D, Oisaki K, Kanai M, Shibasaki M. Tetrahedron Lett. 2006; 47: 1403
18 Chuzel O, Deschamp J, Chausteur C, Riant O. Org. Lett. 2006; 8: 5943
19 Deschamp J, Chuzel O, Hannedouche J, Riant O. Angew. Chem. Int. Ed. 2006; 45: 1292
20 Welle A, Díez-González S, Tinant B, Nolan SP, Riant O. Org. Lett. 2006; 8: 6059
21 Zheng A.-J, Shan F.-J, Li Z.-N, Li Z.-C, Jiang L. Chem. Pap. 2013; 67: 1271
22 Zheng A, Jiang L, Li Z. Chin. J. Chem. 2012; 30: 2587
23 Li Z, Jiang L, Li Z, Chen H. Chin. J. Chem. 2013; 31: 539
24 Du Y, Xu L.-W, Shimizu Y, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 16146
25 For a report on a cobalt-catalyzed aldol addition/lactonization from a maleate monoester monamide, see: Lumby RJ. R, Joensuu PM, Lam HW. Org. Lett. 2007; 9: 4367
26 Chiu P, Li ZN, Fung KC. M. Tetrahedron Lett. 2003; 44: 455
27 Methyl 2-Methyl-5-oxo-2-phenyltetrahydrofuran-3-carboxylate: Typical Procedure A dried Schlenk tube was charged with CuF(PPh₃)₃·2MeOH (5.9 mg, 0.0063 mmol), Xantphos (5.6 mg, 0.0097 mmol), and THF (2.0 mL) under N₂. The mixture was stirred for 30 min and then PMHS (0.15 mL, 2.5 mmol) was added, and the mixture was stirred for a further 15 min. A soln of ketone 3a (84 mg, 0.70 mmol) and dimethyl maleate (137 mg, 0.951 mmol) in THF (2 × 0.5 mL) was added, and the mixture was stirred until 3a was almost consumed (GC). The reaction was quenched by addition of a 0.3 M soln of NH₄F in 3:1 MeOH–H₂O (10 mL). The syn/anti ratio of 4a (66.9:33.1) was then determined by GC. Column chromatography [silica gel, PE–EA (100:0 to 85:15)] gave a diastereomeric mixture of the products as a colorless liquid; yield: 153 mg (93%). Further chromatographic separation gave pure anti-4a and syn-4a. �anti-4a: colorless oil. Rf = 0.50 (EA–PE, 30:70). 1H NMR (400 MHz, CDCl3): δ = 7.46–7.31 (m, 5 H), 3.82 (s, 3 H), 3.60–3.49 (m, 1 H), 2.98 (dd, J = 17.8, 5.1 Hz, 1 H), 2.63 (ddd, J = 17.7, 8.7, 0.9 Hz, 1 H), 1.67 (d, J = 0.8 Hz, 3 H). 13C NMR (101 MHz, CDCl3): δ = 174.42, 171.11, 143.74, 128.84, 128.22, 124.29, 86.96, 52.60, 51.60, 32.04, 25.38. LRMS (EI, 70 ev): m/z (%) = 234 (10, M+), 219 (4), 175 (4), 131 (9), 114 (100), 77 (24), 55 (27), 27 (3). �syn-4a: colorless oil. Rf = 0.43 (EA–PE, 30:70). 1H NMR (400 MHz, CDCl3): d = 7.40–7.24 (m, 5 H), 3.46 (t, J = 7.8 Hz, 1 H), 3.33 (s, 3 H), 3.02 (dd, J = 17.9, 7.0 Hz, 1 H), 2.82 (dd, J = 17.9, 8.7 Hz, 1 H), 1.93 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 174.52, 169.99, 139.83, 128.46, 128.40, 124.91, 87.23, 52.72, 52.08, 32.01, 28.72. LRMS (EI, 70 ev): m/z (%) = 219 (13), 191 (8), 160 (3), 114 (100), 77 (27), 55 (28), 27 (3).�
28 The relative configurations of the 4a diastereoisomers were deduced by base-catalyzed isomerization of the product mixture and by NOSEY spectroscopy. DBU-catalyzed isomerization of mixtures of 4a with syn/anti ratios of 68:32 or 54:46 in refluxing toluene each gave a mixture with a 37:63 syn/anti ratio.
29 Shono T, Hamaguchi H, Nishiguchi I, Sasaki M, Miyamoto T, Miyamoto M, Fujita S. Chem. Lett. 1981; 1217
30 Pohmakotr M, Sampaongoen L, Issaree A, Tuchinda P, Reutrakul V. Tetrahedron Lett. 2003; 44: 6717
31 Pohmakotr M, Komutkul T, Tuchinda P, Prabpai S, Kongsaeree P, Reutrakul V. Tetrahedron 2005; 61: 5311
32 The stereochemistries of the 6a isomers were deduced from their NOESY spectra.