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Synlett

Volumn , Issue 2, 2008, Pages 237-241

Synthesis of substituted allylic sulfonamides from β-alkoxy aziridines and organolithium reagents

(4) Moore, Stephen P a O'Brien, Peter a Whitwood, Adrian C a Gilday, John b

a UNIVERSITY OF YORK (United Kingdom)

b ASTRAZENECA (United Kingdom)

Author keywords

Diastereoselectivity; Lithiation; Organolithium reagents; Stereoselective synthesis; Sulfonamides

Indexed keywords

1 [3 METHYL 1 (TOLUENE 4 SULFONYL) AZIRIDIN 2 YL]BUTAN 1 OL; 4 METHYL N (1 METHYL 2 TRIMETHYLSILANYLMETHYL PROP 2 ENYL)BENZENESULFONAMIDE; AZIRIDINE DERIVATIVE; BETA ALKOXY AZIRIDINE DERIVATIVE; BETA METHOXY N TOSYL AZIRIDINE DERIVATIVE; ORGANOLITHIUM COMPOUND; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOISOMER; LITHIATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 38849104867 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032013 Document Type: Article

Times cited : (10)

References (32)

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20
- 38849090918
- 2O, r.t., 48 h. Using these conditions, allyl alcohol gave the aziridine (24%) and then methyl ether 7 (77%); trans-crotyl alcohol gave the aziridine (90%) and then methyl ether 8 (78%), and prenyl alcohol gave the aziridine (78%) and then methyl ether 7 (66%).
- 2O, r.t., 48 h. Using these conditions, allyl alcohol gave the aziridine (24%) and then methyl ether 7 (77%); trans-crotyl alcohol gave the aziridine (90%) and then methyl ether 8 (78%), and prenyl alcohol gave the aziridine (78%) and then methyl ether 7 (66%).

21
- 38849114541
- 1-[3-Methyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]butan-1-ol (syn-17 and anti-17) Phenyltrimethylammonium tribromide (264 mg, 0.70 mmol) was added to a stirred suspension of Chloramine-T trihydrate (2.17 g, 7.71 mmol) and 2-hepten-4-ol (0.95 mL, 7.01 mmol) in MeCN (35 mL) at r.t. under N2. After stirring the pale yellow suspension at r.t. for 20 h, the solids were removed by filtration through a plug of silica and washed with EtOAc (150 mL, The resulting filtrate was evaporated under reduced pressure to give the crude product, which contained a 75:25 mixture of anti- and syn-17 (by 1H NMR spectroscopy, Purification by flash column chromatography on silica with PE-EtOAc (5:2) as eluent gave syn-17 (436 mg, 22, and anti-17 (1.24 g, 62, both as pale yellow oils. Compound syn-17: Rf, 0.3 (PE-EtOAc, 5:2, IR (CHCl3, 3537 OH
- +: 284.1318; found: 284.1320.

22
- 38849117950
- CCDC reference number 658331.
- CCDC reference number 658331.

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24
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- Yun, J.M.¹ Sim, T.B.² Hahm, H.S.³ Lee, W.K.⁴

25
- 38849145262
- 2O, r.t., 48 h. Yields: anti-10, 85%; syn-10, 60%; anti-11, 60%; syn-11, 64%; anti-12, 14% + 31% starting material + 8% N-Me epoxide from aza-Payne rearrangement; syn-12, 20% + 50% starting material. KHMDS-Mediated-Methylation Conditions: KHMDS, MeI, THF, -78°C (1 h) to r.t. (20 h). Yield: syn-12, 74%; anti-12, 0% + 94% N-Me epoxide from aza-Payne rearrangement.
- 2O, r.t., 48 h. Yields: anti-10, 85%; syn-10, 60%; anti-11, 60%; syn-11, 64%; anti-12, 14% + 31% starting material + 8% N-Me epoxide from aza-Payne rearrangement; syn-12, 20% + 50% starting material. KHMDS-Mediated-Methylation Conditions: KHMDS, MeI, THF, -78°C (1 h) to r.t. (20 h). Yield: syn-12, 74%; anti-12, 0% + 94% N-Me epoxide from aza-Payne rearrangement.

26
- 38849128380
- 4-Methyl-N-(1-methyl-2-trimethylsilanylmethyl-prop-2- enyl)benzenesulfonamide (27) Trimethylsilylmethyllithium (1.31 mL of a 0.72 M solution in pentane, 0.94 mmol) was added dropwise to a stirred solution of aziridine 8 (96 mg, 0.38 mmol) in Et2O (5 mL) at -78°C under Ar. After stirring at -78°C for 5 min, the resulting pale yellow solution was allowed to warm to r.t. over 1 h. Sat. NH4Cl (aq, 5 mL) was then added and the layers were separated. The aqueous layer was extracted with Et2O (3 x 5 mL) and the combined organics were dried (MgSO4) and evaporated under reduced pressure to give the crude product. Purification by flash column chromatography on silica with PE-Et2O (2:1) as eluent gave allylic sulfonamide 27 (71 mg, 61, as a colorless oil; Rf, 0.2 (PE-Et2O, 2:1, IR(CHCl3, 3386 (NH, 2957, 1637, 1599, 1414, 1333 SO
- +: 312.1454; found: 312.1452.

27
- 38849208680
- Characterization Data for 31 White solid, mp 45-46°C. Rf, 0.2 (PE-Et2O, 3:2, IR (CHCl 3, 3327 (NH, 2927, 1450, 1324 (SO2, 1162 (SO 2, 1091 cm-1. 1H NMR (400 MHz, CDCl 3, δ, 7.73 (d, J, 8.0 Hz, 2 H, 2-C6H 4SO2, 7.28 (d, J, 8.0 Hz, 2 H, 3-C 6H4SO2, 5.93 (s, 1 H, NH, 3.60 (s, 2 H, CH2O, 3.11 (s, 3 H, OMe, 2.42 (s, 3 H, ArMe, 1.71 (s, 6 H, 2 x Me, 13C NMR (100.6 MHz, CDCl3, δ, 143.4 (ipso-C6H4SO2, 137.9 (ipso- C6H4Me, 136.7, C, 129.5 (2-C6H 4SO2, 127.3 (3-C6H4Me, 123.6, CNH, 69.1 (CH2O, 57.8 (OMe, 21.5 (ArMe, 20.6 (Me, 19.7 (Me, MS (CI, NH3, m/z, 270 45
- +: 270.1164; found: 270.1161.

28
- 34247133497
- Doris, E.; Dechoux, L.; Mioskowski, C. Chem. Commun. 1996, 549.
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- Doris, E.¹ Dechoux, L.² Mioskowski, C.³

29
- 38849194280
- Characterization Data for 32 White solid, mp 91-92°C Rf, 0.2 (PE-Et2O, 3:2, IR (CHCl 3, 3306 (NH, 3019, 1382, 1328 (SO2, 1149 (SO 2, 1093 cm-1. 1H NMR (400 MHz, CDCl 3, δ, 7.81 (d, J, 8.0 Hz, 2 H, 2-C6H 4SO2, 7.28 (d, J, 8.0 Hz, 2 H, 3-C 6H4SO2, 5.25 (NH, 2.42 (s, 3 H, ArMe, 2.09 (s, 1 H, CH, 1.54 (s, 6 H, 2 x Me, 13C NMR (100.6 MHz, CDCl3, δ, 143.1 (ipso-C6H 4SO2, 138.8(ipso-C6H4Me, 129.2 (2-C6H4SO2, 127.6 (3-C6H 4SO2, 85.3 (CH, 71.2 (C, 49.8 (CN, 30.6 (2 x Me, 21.5 (ArMe, MS (CI, NH3, m/z, 255 (100, M, NH 4, 238 (46, 189 (60, HRMS CI, N
- +: 255.1167; found: 255.1160.

30
- 38849189583
- Characterization Data for 33 White solid, mp 74-75°C. Rf, 0.1 (PE-Et2O, 3:2, IR (CHCl3, 3306 (NH, 3019, 1571, 1327 (SO2, 1163 (SO2, 1092 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.74 (d, J, 8.0 Hz, 2 H, 2-C6H4SO2, 7.27 (d, J, 8.0 Hz, 2 H, 3-C6H4SO2, 6.36 (d, J, 13.0 Hz, 1 H, CHO, 4.73 (s, 1 H, NH, 4.57 (d, J, 13.0 Hz, 1 H, CH, 3.26 (s, 3 H, OMe, 2.42 (s, 3 H, ArMe, 1.35 (s, 6 H, 2 x Me, 13C NMR (100.6 MHz, CDCl3, δ, 147.7, CH, 142.8 (ipso-C6H4SO2, 140.2 (ipso-C6H4Me, 129.3 (2-C6H 4SO2, 127.2 (3-C6H4SO2, 108.6, CH, 58.0 (CN, 55.4 (OMe, 29.2 (2 x Me, 21.5 (ArMe, MS CI, NH3
- +: 270.1164; found: 270.1158..

31
- 0001072368
- Hodgson, D. M.; Stent, M. A. H.; Wilson, F. X. Org. Lett. 2001, 3, 3401.
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- Hodgson, D.M.¹ Stent, M.A.H.² Wilson, F.X.³

32
- 34447529183
- Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 8432
- Barchuk, A.¹ Ngai, M.-Y.² Krische, M.J.³

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