Enantioselective conjugate radical addition to α'-phenylsulfonyl enones

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 4947-4949

  Lee, Jin Young ^a   Kim, Sundae ^b   Kim, Sunggak ^a,b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; OXAZOLINE DERIVATIVE; SULFONE DERIVATIVE; ZINC;

ADDITION REACTION; ARTICLE; CATALYST; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 78549259661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.014     Document Type: Article

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24. 2O solution (2 mL) of α-phenylsulfonyl enone 6 (28 mg, 0.10 mmol) was added via cannula.
25. The mixture was stirred for 30 min, the reaction mixture was cooled down to -78 °C and then isopropyl iodide (100 μL, 1.0 mmol), tributyltin hydride (83 μL, 0.30 mmol), and triethylborane (200 μL, 0.20 mmol) were added sequentially.
26. After the reaction was stirred at -78 °C under a balloon of air for 12 h, the solvent was evaporated and the residue was filtered through a short column of KF/silica gel (1/9 w/w) to remove organotin residue.
27. The filtrate was concentrated and subjected to silica gel column chromatography to give 7 (30.5 mg, 92%).
28. 3, 400 MHz) δ 0.65 (d, J = 6.9 Hz, 3H), 0.87 (d, J = 6.9 Hz, 3H), 1.74- 1.80 (m, 1H), 2.74-2.80 (m, 1H), 2.97 (dd, J = 17.2, 4.4 Hz, 1H), 3.15 (dd, J = 17.2, 10.3 Hz, 1H), 3.77 (d, J = 13.3 Hz, 1H), 3.92 (d, J = 13.3 Hz, 1H), 7.06 (d, J = 6.9 Hz, 2H), 7.13 (d, J = 6.9 Hz, 1H), 7.19-7.22 (m, 2H), 7.37 (t, J = 7.8 Hz, 2H), 7.52 (t, J = 7.8 Hz, 2H), 7.51-7.53 (m, 1H);
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