8-Quinolinyl Oxazoline: Ligand Exploration in Enantioselective Ni-Catalyzed Reductive Carbamoyl-Alkylation of Alkene to Access the Chiral Oxindoles

Baixue Luan; Zaiquan Tang; Xianqing Wu; Yifeng Chen

doi:10.1055/a-1863-8957

Synlett, Inhaltsverzeichnis

Synlett 2022; 33(18): 1847-1852
DOI: 10.1055/a-1863-8957

cluster

Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

8-Quinolinyl Oxazoline: Ligand Exploration in Enantioselective Ni-Catalyzed Reductive Carbamoyl-Alkylation of Alkene to Access the Chiral Oxindoles

Baixue Luan

,

Zaiquan Tang

,

Xianqing Wu∗

,

Yifeng Chen ∗

Abstract

Alle Artikel dieser Rubrik

Abstract

Chiral ligands play an essential role in transition-metal-catalyzed enantioselective transformations, in which chiral oxazoline-based scaffolds are the privileged chiral ligand. Nevertheless, 8-quinolinyl oxazoline (8-Quinox) ligands are underexplored in transition-metal-catalyzed asymmetric transformations since their development in 1998. Herein, we report an 8-Quinox ligand promoted Ni-catalyzed enantioselective reductive carbamoyl-alkylation of carbamoyl chloride tethered styrene with unactivated alkyl iodide, providing an expedient access to valuable enantioenriched oxindoles in good results.

Key words

chiral ligand - nickel catalysis - reductive coupling - dicarbofunctionalization of alkene - oxindole

Volltext

Referenzen

References and Notes

1a Feng J, Holmes M, Krische MJ. Chem. Rev. 2017; 117: 12564
1b Süsse L, Stoltz BM. Chem. Rev. 2021; 121: 4084

2 For a selected book, see: Privileged Chiral Ligands and Catalysts . Zhou Q.-L. Wiley-VCH; Weinheim: 2011

3a Hargaden GC, Guiry PJ. Chem. Rev. 2009; 109: 2505
3b Carroll MP, Guiry PJ. Chem. Soc. Rev. 2014; 43: 819
3c Yang G, Zhang W. Chem. Soc. Rev. 2018; 47: 1783
3d Connon R, Roche B, Rokade BV, Guiry PJ. Chem. Rev. 2021; 121: 6373

4a Brunner H, Obermann U, Wimmer P. J. Organomet. Chem. 1986; 316: C1
4b Brunner H, Obermann U, Wimmer P. Organometallics 1989; 8: 821

For selected examples, see:

5a Werner EW, Mei TS, Burckle AJ, Sigman MS. Science 2012; 338: 1455
5b Mei TS, Werner EW, Burckle AJ, Sigman MS. J. Am. Chem. Soc. 2013; 135: 6830
5c Mei TS, Patel HH, Sigman MS. Nature 2014; 508: 340
5d Patel HH, Sigman MS. J. Am. Chem. Soc. 2015; 137: 346
5e Bahamonde A, Al Rifaie B, Martín-Heras V, Allen JR, Sigman MS. J. Am. Chem. Soc. 2019; 141: 8708
5f Liu J, Yuan Q, Toste FD, Sigman MS. Nat. Chem. 2019; 11: 710
5g Ross SP, Rahman AA, Sigman MS. J. Am. Chem. Soc. 2020; 142: 10516

6 Nishiyama H, Sakaguchi H, Nakamura T, Horihata M, Kondo M, Itoh K. Organometallics 1989; 8: 846

7a Zhang L, Zuo Z.-Q, Wan X.-L, Huang Z. J. Am. Chem. Soc. 2014; 136: 15501
7b Chen J, Xi T, Lu Z. Org. Lett. 2014; 16: 6452

8 Babu SA, Krishnan KK, Ujwaldev SM, Anilkumar G. Asian J. Org. Chem. 2018; 7: 1033
9 Chen J, Xi T, Lu Z. Org. Chem. Front. 2018; 5: 247 ; and the references therein

10a Wu X.-Y, Li X.-H, Zhou Q.-L. Tetrahedron: Asymmetry 1998; 9: 4143
10b Wu X.-Y, Xu H.-D, Zhou Q.-L, Chan AS. C. Tetrahedron: Asymmetry 2000; 11: 1255
10c Li X.-G, Cheng X, Ma J.-A, Zhou Q.-L. J. Organomet. Chem. 2001; 640: 65
10d Wu X.-Y, Xu H.-D, Tang F.-Y, Zhou Q.-L. Tetrahedron: Asymmetry 2001; 12: 2565
10e Li Z.-P, Wu X.-Y, Zhou Q.-L, Chan W.-L. Chin. J. Chem. 2001; 19: 40
10f Zhou Y.-B, Tang F.-Y, Xu H.-D, Wu X.-Y, Ma J.-A, Zhou Q.-L. Tetrahedron: Asymmetry 2002; 13: 469

11a Lu P, Ren X, Xu H, Lu D, Sun Y, Lu Z. J. Am. Chem. Soc. 2021; 143: 12433
11b Ren X, Lu Z. Org. Lett. 2021; 23: 8370

For selected reviews and examples, see:

12a Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
12b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
12c Trost BM, Brennan MK. Synthesis 2009; 18: 3003
12d Huters AD, Styduhar ED, Garg NK. Angew. Chem. Int. Ed. 2012; 51: 3758
12e Kato H, Yoshida T, Tokue T, Nojiri Y, Hirota H, Ohta T, Williams RM, Tsukamoto S, Notoamides A.-D. Angew. Chem. Int. Ed. 2007; 46: 2254

For selected reviews and examples, see:

13a Cao Z.-Y, Zhou F, Zhou J. Acc. Chem. Res. 2018; 51: 1443
13b Ping Y, Li Y, Zhu J, Kong W. Angew. Chem. Int. Ed. 2019; 58: 1562
13c Marchese AD, Larin EM, Mirabi B, Lautens M. Acc. Chem. Res. 2020; 53: 1605
13d Hu HZ, Teng F, Liu J, Hu WM, Luo S, Zhu Q. Angew. Chem. Int. Ed. 2019; 58: 9225
13e Bai X, Wu C, Ge S, Lu Y. Angew. Chem. Int. Ed. 2020; 59: 2764

For selected reviews and examples, see:

14a Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
14b Jin Y, Wang C. Angew. Chem. Int. Ed. 2019; 58: 6722
14c Tian Z.-X, Qiao J.-B, Xu G.-L, Pang X, Qi L, Ma W.-Y, Zhao Z.-Z, Duan J, Du Y.-F, Su P, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2019; 141: 7637
14d Peng Y, Wang K, Pan Q, Ding Z, Zhou Z, Guo Y, Kong W. ACS Catal. 2019; 9: 7335
14e Li Y, Ding Z, Lei A, Kong W. Org. Chem. Front. 2019; 6: 3305
14f Ma T, Chen Y, Li Y, Ping Y, Kong W. ACS Catal. 2019; 9: 9127
14g Jin Y, Yang H, Wang C. Org. Lett. 2019; 21: 7602
14h Jin Y, Wang C. Chem. Sci. 2019; 10: 1780
14i He J, Xue Y, Han B, Zhang C, Wang Y, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 2328
14j Fan P, Lan Y, Zhang C, Wang C. J. Am. Chem. Soc. 2020; 142: 2180
14k Chen X.-W, Yue J.-P, Wang K, Gui Y.-Y, Niu Y.-N, Liu J, Ran C.-K, Kong W, Zhou W.-J, Yu D.-G. Angew. Chem. Int. Ed. 2021; 60: 14068
14l Qiao J.-B, Zhang Y.-Q, Yao Q.-W, Zhao Z.-Z, Peng X, Shu X.-Z. J. Am. Chem. Soc. 2021; 143: 12961
14m Wu J, Wang C. Org. Lett. 2021; 23: 6407

15 Lan Y, Wang C. Commun. Chem. 2020; 3: 45

16a Wu X, Qu J, Chen Y. J. Am. Chem. Soc. 2020; 142: 15654
16b Wu X, Luan B, Zhao W, He F, Wu X.-Y, Qu J, Chen Y. Angew. Chem. Int. Ed. 2022; in press
16c Wu X, Shrestha M, Chen Y. Synlett 2021; 32: 955
16d He Y, Zhu S. Chin. J. Org. Chem. 2020; 40: 4377
16e Shrestha M, Wu X, Huang W, Qu J, Chen Y. Org. Chem. Front. 2021; 8: 4024

17a Fang K, Huang W, Shan C, Qu J, Chen Y. Org. Lett. 2021; 23: 5523
17b Huang W, Shrestha M, Wang C, Fang K, Teng Y, Qu J, Chen Y. Org. Chem. Front. 2021; 8: 4106
17c Xi Y, Wang C, Zhang Q, Qu J, Chen Y. Angew. Chem. Int. Ed. 2021; 60: 2699

18 General Procedure To a dried 8 mL vial were added ligand (22 mol%), Mn (2.0 equiv), Ni(ClO₄)₂ ·6H₂O (15 mol%), and carbamoyl chloride (1.0 equiv) (if solid). Then the vial was transferred into glovebox. LiBr (1.0 equiv), NMP (0.2 M), carbamoyl chloride (1.0 equiv) (if liquid), and alkyl halide (3.0 equiv) were added in sequence inside the glovebox. The vial was then put into the glovebox and stirred for the needed time. After completion, the reaction mixture was quenched with H₂O, filtered through a pad of Celite, and extracted with EtOAc for three times. The resulted filtrate was separated. The combined organic phase was washed with brine and concentrated under reduced pressure to yield the crude product, which was purified by silica gel flash column chromatography to afford products 3. (S)-1,3-Dimethyl-3-octylindolin-2-one (3a) Pale yellow oil (31.6 mg, 58%); R_f = 0.56 (PE/EtOAc = 10:1); [α]_D ²³ + 7.90 (c = 1.67, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 7.26 (td, J = 8.0, 1.2 Hz, 1 H), 7.16 (dd, J = 7.2, 0.8 Hz, 1 H), 7.06 (td, J = 7.6, 0.8 Hz, 1 H), 6.84 (d, J = 7.6 Hz, 1 H), 3.21 (s, 3 H), 1.88 (td, J = 12.4, 4.8 Hz, 1 H), 1.71 (td, J = 12.4, 4.4 Hz, 1 H), 1.34 (s, 3 H), 1.25–1.14 (m, 10 H), 1.00–0.77 (m, 5 H). ¹³C NMR (100 MHz, CDCl₃): δ = 181.0, 143.5, 134.5, 127.7, 122.6, 122.5, 108.0, 48.6, 38.7, 31.9, 29.9, 29.4, 29.3, 26.2, 24.6, 23.9, 22.7, 14.2. HRMS (ESI): m/z calcd for C₁₈H₂₈NO⁺: 274.2165; found: 274.2157. HPLC (Chiralpak IC): n-hexane/i-PrOH = 90:10, flow rate 1.0 mL/min, λ = 254 nm, t _R = 6.551 min (major), t _R = 8.110 min (minor); 96:4 e.r. (S)-1-Benzyl-3-methyl-3-octylindolin-2-one (3b) Pale yellow oil (38.1 mg, 55%); R_f = 0.77 (PE/EtOAc = 10:1); [α]_D ²³ + 10.30 (c = 0.66, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 7.29–7.23 (m, 5 H), 7.12 (dd, J = 16.8, 7.8 Hz, 2 H), 7.00 (t, J = 7.2 Hz, 1 H), 6.69 (d, J = 7.6 Hz, 1 H), 4.97 (d, J = 15.6 Hz, 1 H), 4.82 (d, J = 15.6 Hz, 1 H), 1.93 (td, J = 12.0, 2.8 Hz, 1 H), 1.74 (td, J = 12.8, 3.2 Hz, 1 H), 1.38 (s, 3 H), 1.23–1.13 (m, 12 H), 0.82 (t, J = 7.2 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 181.1, 142.5, 136.3, 134.4, 128.8, 127.6, 127.4, 122.7, 122.5, 109.1, 48.6, 43.7, 38.7, 31.9, 29.9, 29.4, 29.3, 24.8, 24.3, 22.7, 14.2. HRMS (ESI): m/z calcd for C₂₄H₃₂NO⁺: 350.2478; found: 350.2470. HPLC (Chiralpak IC): n-hexane/i-PrOH = 90:10, flow rate 1.0 mL/min, λ = 254 nm, t _R = 5.739 min (major), t _R = 6.239 min (minor); 95.5:4.5 e.r. (S)-1,3-Dimethyl-3-octyl-6-(trifluoromethyl)indolin-2-one (3c) Pale yellow oil (30.7 mg, 45%); R_f = 0.65 (PE/EtOAc = 10:1); [α]_D ²³ + 13.76 (c = 2.95, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 7.27 (d, J = 7.2 Hz, 1 H), 7.18 (d, J = 7.6 Hz, 1 H), 6.96 (s, 1 H), 3.17 (s, 3 H), 1.83 (td, J = 12.0, 3.2 Hz, 1 H), 1.66 (td, J = 12.0, 3.6 Hz, 1 H), 1.28 (s, 3 H), 1.17–1.07 (m, 12 H), 0.76 (t, J = 6.4 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 180.6, 144.1, 138.4, 130.2 (q, J _C–F = 32.3 Hz), 124.1 (q, J _C–F = 270.2 Hz), 122.7, 119.6 (q, J _C–F = 3.8 Hz), 104.6 (q, J _C–F = 3.7 Hz), 48.7, 38.5, 31.9, 29.8, 29.3, 29.3, 26.4, 24.6, 23.7, 22.7, 14.2. ¹⁹F NMR (376 MHz, CDCl₃): δ = –62.3; HRMS (ESI): m/z calcd for C₁₉H₂₇F₃NO⁺: 342.2039; found: 342.2030. HPLC (Chiralpak IC): n-hexane/i-PrOH = 90:10, flow rate 1.0 mL/min, λ = 254 nm, t _R = 4.627 min (major), t _R = 5.098 min (minor); 95.5:4.5 e.r. ( S )-1,3-Dimethyl-3-propylindolin-2-one (3d) Pale yellow oil (29.7 mg, 73%); R_f = 0.42 (PE/EtOAc = 10:1); [α]_D ²³ +15.04 (c = 2.78, CHCl₃). ¹H NMR (400 MHz, CDCl₃): δ = 7.26 (t, J = 8.0 Hz, 1 H), 7.17 (d, J = 7.2 Hz, 1 H), 7.06 (t, J = 7.6 Hz, 1 H), 6.83 (d, J = 7.2 Hz, 1 H), 3.21 (s, 3 H), 1.88 (td, J = 12.4, 4.4 Hz, 1 H), 1.70 (td, J = 12.0, 4.0 Hz, 1 H), 1.35 (s, 3 H), 1.05–0.96 (m, 1 H), 0.90–0.83 (m, 1 H), 0.77 (t, J = 7.2 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 181.0, 143.4, 134.4, 127.7, 122.6, 122.5, 107.9, 48.6, 40.9, 26.2, 23.8, 17.9, 14.3. HRMS (ESI): m/z calcd for C₁₃H₁₈NO⁺: 204.1383; found: 204.1378. HPLC (Chiralpak IC): n-hexane/i-PrOH = 90:10, flow rate 1.0 mL/min, λ = 254 nm, t _R = 7.967 min (major), t _R = 8.377 min (minor); 91.5:8.5 e.r.

Zusatzmaterial

Supporting Information