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Synlett

Volumn , Issue 6, 2008, Pages 827-830

A versatile entry to 3-unsubstituted 2-isoxazolines

(2) Pohjakallio, Antti a Pihko, Petri M a

a AALTO UNIVERSITY (Finland)

Author keywords

Aldehydes; Catalysis; Heterocycles; Isoxazoline; Oximes

Indexed keywords

2 ISOXAZOLINE DERIVATIVE; ALIPHATIC COMPOUND; ANILINIUM DERIVATIVE; OXIME DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; METHODOLOGY; SYNTHESIS;

EID: 42049084827 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042900 Document Type: Article

Times cited : (10)

References (25)

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2
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- For examples of the use of 2-isoxazolines in total synthesis setting, see: Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410
- (b) For examples of the use of 2-isoxazolines in total synthesis setting, see: Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.

3
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8
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- Jacquier, R.¹ Olive, J.-L.² Petrus, C.³ Petrus, F.⁴

9
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12
- 0010695841
- Acetone oxime has previously been used as a transoximation reagent. See
- Acetone oxime has previously been used as a transoximation reagent. See: Juskowiak, M.; Krzyzanowski, P. J. Prakt. Chem. 1989, 331, 870.
- (1989) J. Prakt. Chem , vol.331 , pp. 870
- Juskowiak, M.¹ Krzyzanowski, P.²

13
- 42049094881
- For the preparation of volatile 10a, the use of acetaldehyde oxime under modified conditions is recommended. See ref. 21.
- For the preparation of volatile 10a, the use of acetaldehyde oxime under modified conditions is recommended. See ref. 21.

14
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- Erkkilä, A.; Pihko, P. M.; Clarke, M.-R. Adv. Synth. Catal. 2007, 349, 802.
- (2007) Adv. Synth. Catal , vol.349 , pp. 802
- Erkkilä, A.¹ Pihko, P.M.² Clarke, M.-R.³

15
- 42049088948
- In control experiments, the reaction products did not equilibrate to starting materials when exposed to the reaction conditions [e.g, 3-pentanone (30 mol, catalyst 50 mol, r.t, 3 h
- In control experiments, the reaction products did not equilibrate to starting materials when exposed to the reaction conditions [e.g., 3-pentanone (30 mol%), catalyst (50 mol%), r.t., 3 h].

16
- 34548254475
- A related reaction for the preparation of 3-substituted 2-isoxazolines from β,γ-unsaturated ketones has been proposed to follow this mechanism. See: Norman, A. L.; Shurrush, K. A.; Calleroz, A. T.; Mosher, M. D. Tetrahedron Lett. 2007, 48, 6849.
- A related reaction for the preparation of 3-substituted 2-isoxazolines from β,γ-unsaturated ketones has been proposed to follow this mechanism. See: Norman, A. L.; Shurrush, K. A.; Calleroz, A. T.; Mosher, M. D. Tetrahedron Lett. 2007, 48, 6849.

17
- 42049104140
- We initially believed that this species is hydroxylamine. However, in control experiments, hydroxylammonium diphenylphosphate turned out to be relatively poor catalyst for the reaction, and exhibited a similar induction period than acid catalysts
- We initially believed that this species is hydroxylamine. However, in control experiments, hydroxylammonium diphenylphosphate turned out to be relatively poor catalyst for the reaction, and exhibited a similar induction period than acid catalysts.

18
- 42049115673
- Moderate enantioselectivities (up to 63%) could be obtained using a chiral imidazolidinone base along with strong acids in colder temperatures. However, in these cases, the reaction rate and conversion were poor. Attempts to obtain enantioenriched products in the presence of chiral phosphoric acids failed. These studies will be reported separately.
- Moderate enantioselectivities (up to 63%) could be obtained using a chiral imidazolidinone base along with strong acids in colder temperatures. However, in these cases, the reaction rate and conversion were poor. Attempts to obtain enantioenriched products in the presence of chiral phosphoric acids failed. These studies will be reported separately.

19
- 42049115674
- Gibert, J. P.; Jacquier, R.; Pétrus, C. Bull. Soc. Chim. Fr. 1979, 281.
- (1979) Bull. Soc. Chim. Fr , pp. 281
- Gibert, J.P.¹ Jacquier, R.² Pétrus, C.³

20
- 42049106627
- General Procedure for the Preparation of 2-Isoxazolines Using Diethylketone Oxime To a solution of amine salt 11 (37.1 mg, 0.1 mmol, 20.7 mol, in toluene (2.5 mL) at 0°C was added aldehyde (0.6 mmol, 120 mol, After 4 min, diethylketone oxime (55 μL, 0.5 mmol, 100 mol, was added and the mixture was stirred at 0°C for the indicated period of time. The reaction mixture was diluted with Et2O, 15 mL, washed with sat. NaHCO3 (5 mL, and 5% oxalic acid (2 x 5 mL, The layers were separated. The acidic and basic aqueous layers were back-extracted separately with Et2O (2 x 6 mL and 5 mL, respectively, The combined organic layers were washed with brine, dried Na2SO4, and concentrated to a of 1-2 mL. The residue was purified by column chromatography
- 4), and concentrated to a volume of 1-2 mL. The residue was purified by column chromatography.

21
- 42049106626
- Analytical Data of Compound 10c Reaction time: 6.5 h; yield 0.076 g (86, eluent: gradient: 10-30% MTBE in hexane; Rf, 0.35 (40% EtOAc in hexane, IR (film, 3062, 3026, 2924, 2589, 1600, 1495, 1454, 1275, 843 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.31-7.27 (m, 2 H, 7.21-7.18 (m, 3 H, 7.12 (t, 1 H, J, 1.8 Hz, 4.52 (m, 1 H, 3.04 (ddd, 1 H, J1, 1.8 Hz, J 2, 10.5 Hz, J3, 17.4 Hz, 2.80 (ddd, 1 H, J1, 5.6 Hz, J2, 9.5 Hz, J 3, 13.9 Hz, 2.72 (ddd, 1 H, J1, 6.9 Hz, J2, 9.3 Hz, J3, 13.9 Hz, 2.62 (ddd, 1 H, J1, 1.8 Hz, J2, 7.8 Hz, J 3, 17.4 Hz, 2.01 (dddd, 1 H, J1, 5.6 Hz, J2, 7.9 Hz, J3, 9.3 Hz, J 4, 13.6 Hz, 1.83 dd
- 13NO + H]: 176.1075; found: 176.1070.

22
- 42049092778
- Analytical Data of Compound 10d Reaction time: 15.5 h; yield 0.061 g (63, eluent: 10-30% MTBE in hexane; Rf, 0.25 (50% EtOAc in hexane, IR (film, 3419, 3064, 3031, 2918, 2852, 1726, 1602, 1496, 1453, 1367, 1114, 1027, 838 cm-1. 1H NMR (400 MHz, CDCl 3, δ, 7.37-7.27 (m, 5 H, 7.12 (t, 1 H, J, 1.8 Hz, 4.71 (dtdd, 1 H, J1, 0.5 Hz, J2, 5.0 Hz, J3, 7.4 Hz, J4, 10.7 Hz, 4.58 (s, 2 H, 3.58 (dd, 1 H, J1, 5.0 Hz, J2, 10.4 Hz, 3.52 (dd, 1 H, J1, 5.0 Hz, J2, 10.4 Hz, 3.04 (ddd, 1 H, J1, 1.8 Hz, J2, 10.7 Hz, J3, 17.6 Hz, 2.90 (ddd, 1 H, J1, 1.8 Hz, J2, 7.4 Hz, J3, 17.6 Hz, 13C NMR 100 MHz, CDCl3, δ, 145.8, 137.8, 128.4, 1
- 2 + H]: 192.1025; found: 192.1028.

23
- 42049115101
- Analytical Data of Compound 10h Reaction time: 15 h; yield 0.072 g (73, eluent: gradient 50-65% MTBE in hexane; Rf, 0.23 (30% MTBE in hexane, IR (film, 2949, 2862, 2738, 1723, 1690, 1657, 1436, 1273, 1161, 1128, 974 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.11 (t, 1 H, J, 1.7 Hz, 6.93 (td, 1 H, J1, 7.0 Hz, J2, 15.6 Hz, 5.82 (td, 1 H, J1, 1.6 Hz, J2, 15.6 Hz, 4.50 (m, 1 H, 3.70 (s, 3 H, 3.05 (ddd, 1 H, J1, 1.8 Hz, J2, 10.5 Hz, J3, 17.4 Hz, 2.60 (ddd, 1 H, J1, 1.8 Hz, J2, 7.9 Hz, J3, 17.4 Hz, 2.25 (m, 2 H, 1.72-1.47 (m, 4 H, 13C NMR (100 MHz, CDCl3, δ, 166.9, 148.6, 145.8, 121.4, 78.2, 51.4, 40.5, 34.5, 31.8, 24.0. HRMS ESI , m/z calcd for [C10H15NO
- 3 + Na]: 220.0950; found: 220.0946.

24
- 42049106624
- Synthesis of Compound 10b To a solution of salt 11 (0.743 g, 2.08 mmol, 10.4 mol, in CHCl3 (50 mL) at 0°C was added crotonaldehyde (1.99 mL, 24 mmol, 120 mol, After 6 min, acetaldehyde oxime (1.23 mL, 20 mmol, 100 mol, was added. The ice bath was removed and the reaction mixture was stirred at r.t. After 6 h, the reaction mixture was washed with 10% oxalic acid solution (10 mL) and then with 5% oxalic acid (30 mL, 20 mL, Hexanes (10 mL) was added22 and the layers were separated. The organic layer was washed with sat. NaHCO3 (20 mL) and both acidic and basic aqueous phases were back-extracted separately with Et2O (50 mL, The combined organic phases were dried (Na2SO4) and concentrated by distillation. The dark brown residue was distilled under reduced pressure (15 mmHg, water-aspirator vacuum) to give 0.871 g (51, of 10b as colorless liquid purity >95% by 1H NMR, Analytic
- 7NO - H]: 84.0449; found: 84.0453.

25
- 42049121185
- The catalyst is highly soluble in chlorinated solvents, but less soluble in hydrocarbons. Addition of hexanes assists in catalyst removal. The same yield has also been obtained in 50 mmol scale by direct distillation of the reaction mixture, without attempts to remove the catalyst components.
- The catalyst is highly soluble in chlorinated solvents, but less soluble in hydrocarbons. Addition of hexanes assists in catalyst removal. The same yield has also been obtained in 50 mmol scale by direct distillation of the reaction mixture, without attempts to remove the catalyst components.

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