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Synlett

Volumn , Issue 4, 2007, Pages 615-618

Yb(OTf)3-catalyzed [4+2] cycloaddition of allenyltrimethylsilylthioketenes with arylaldimines

(4) Aoyagi, Shigenobu a Ohata, Satoru a Shimada, Kazuaki a Takikawa, Yuji a

a IWATE UNIVERSITY (Japan)

Author keywords

4+2 cycloaddition; Allenyltrimethylsilylthioketene; Arylaldimine; Onychine; Yb(OTf)3

Indexed keywords

4 AZAFLUORENONE; ALLENYLTRIMETHYLSILYLTHIOKETENE DERIVATIVE; ARYLALDIMINE DERIVATIVE; FLUORENONE DERIVATIVE; IMINE; KETENE DERIVATIVE; LACTAM DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; SYNTHESIS;

EID: 33947314494 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970748 Document Type: Article

Times cited : (10)

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33
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- To a CHCl3 (30 mL) solution of 4f (500 mg, 1.03 mmol) was added N-tosyl-3-phenyloxaziridine (340 mg, 1.23 mmol) portionwise at 0°C and then the solution was stirred at r.t. for 30 min. The reaction was quenched with an excess amount of aq Na2SO3 solution and the organic layer was separated and dried over anhyd Na2SO 4. After evaporation of the solvent, the residue was subjected to column chromatography on silica gel (hexane-EtOAc, 7:1, 6f: yield: 325 mg (67, colorless oil. MS: m/z, 469 (19, M, 454 (19, M, Me, 121 (100, PMB, IR (neat, 2951, 1625, 1512, 1247, 1036, 845 cm-1. 1H NMR (400 MHz, CDCl3, δ, 0.39 (s, 9 H, 1.99 (s, 3 H, 3.47 (d, J, 14.6 Hz, 1 H, 3.78 (s, 3 H, 5.22 (d, J, 14.6 Hz, 1 H, 5.28 (s, 1 H, 5.55 (s, 1 H, 5.59 (s, 1 H, 6.81 (d, J, 6.6 Hz, 2 H, 7.10-7.20 (m, 1 H, 7.22 d
- 2Si: C, 61.27; H, 6.00; N, 2.98. Found: C, 61.09; H, 6.07; N, 2.97.

34
- 33947327749
- A DMF solution (10 mL) of 6f (300 mg, 64 mmol, tri(o-toly)phosphine (19 mg, 6 mmol, Pd(OAc)2 (7 mg, 3 mmol) and Et3N (323 mg, 320 mmol) was stirred at 90°C for 12 h under a N2 atmosphere. After removal of DMF by distillation under reduced pressure, the residue was subjected to column chromatography on silica gel (hexane-EtOAc, 7:1, 7f: yield: 144 mg (58, pale yellow plates; mp 142.7-144.0°C. MS: m/z, 389 (42, M, 374 (23, M+-Me, 121 (100, PMB, IR (KBr, 2951, 1619, 1579, 1247, 850 cm-1. 1H NMR (400 MHz, CDCl3, δ, 0.39 (s, 9 H, 2.40 (s, 3 H, 3.62 (s, 2 H, 3.73 (s, 3 H, 5.66 (br s, 2 H, 6.80 (d, J, 8.2 Hz, 2 H, 7.09 (d, J, 8.2 Hz, 2 H, 7.21 (t, J, 7.6 Hz, 1 H, 7.28 (t, J, 7.4 Hz, 1 H, 7.51 (d, J, 7.4 Hz, 1 H, 7.58 (d, J, 7.9 Hz, 1 H, 13C NMR 100 MHz, CDCl 3
- 2Si: C, 74.00; H, 6.99; N, 3.60. Found: C, 73.83; H, 7.15; N, 3.65.

35
- 33947310297
- A CHCl3 (30 mL) solution of 7f (120 mg, 31 mmol) and p-toluenesulfonic acid monohydrate (205 mg, 108 mmol) was heated to reflux for 5 h. The reaction was quenched with an excess amount of aq NaHCO 3 solution and the organic layer was separated and dried over anhyd Na2SO4. After evaporation of the solvent, the residue was subjected to column chromatography on silica gel (hexane-EtOAc, 7:1, 8f: yield: 86 mg (88, pale yellow solid; mp 162.2-163.8°C (lit.7g 164-165°C, MS: m/z(, 317 (10, M, 121 (100, PMB, IR (KBr, 2956, 1651, 1526, 1516, 1252, 1174, 1032, 842 cm-1. 1H NMR (400 MHz, CDCl3, δ, 2.32 (s, 3 H, 3.62 (s, 2 H, 3.73 (s, 3 H, 5.71 (br s, 2 H, 6.48 (s, 1 H, 6.82 (d, J, 8.6 Hz, 2 H, 7.12 (d, J, 8.6 Hz, 2 H, 7.25-7.35 (m, 2 H, 7.54 (d, J, 7.1 Hz, 1 H, 7.62 d, J, 7.6 Hz, 1 H, 13C
- 3): δ = 19.0 (q),33.6 (t), 46.8 (t), 55.2 (q), 114.2(d), 116.6(d), 121.9 (s), 122.5 (d), 125.2 (d), 127.07 (d), 127.13 (d), 127.4 (d), 128.2 (s), 136.3 (s), 144.4 (s), 145.6 (s), 147.5 (s), 158.6 (s), 163.7 (s).

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