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(R)-Nifenalol (2)8,24
4 For selected examples, see: (a) Y. Huang, A. M. Walji,
C. H. Larsen and D. W. C. MacMillan, J. Am. Chem. Soc.,
White solid. 1H NMR (300 MHz, CDCl3): d ¼ 8.16 (d, 2H, J ¼ 8.4
Hz), 7.51 (d, 2H, J ¼ 8.5 Hz), 4.82 (dd, 1H, J ¼ 3.2, and 9.2 Hz),
2.96 (dd, 1H, J ¼ 3.4, and 12.2 Hz), 2.40–2.64 (m, 1H), 2.60 (dd,
1H, J ¼ 9.3, and 12.2 Hz), 1.11 (d, 3H, J ¼ 6.7 Hz), 1.10 (d, 3H, J ¼
6.7 Hz). 13C-NMR (300 MHz, CDCl3): d ¼ 149.9, 146.8, 126.0,
123.2, 70.4, 53.7, 48.4, 22.7, 22.4. MS (EI) m/z (%): 151 (5), 72
(100). Chiral HPLC (Chiralpak IC, n-hexane–2-PrOH–triethyl-
amine 94.9 : 5 : 0.1, ow rate 0.5 mL minꢁ1, l ¼ 280 nm): tR 25.1
min (R), 26.5 min (S).
¨
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R. Rios, J. Vesely, L. Eriksson and A. Cordova, Angew.
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8468; (d) S. Belot, K. A. Vogt, C. Besnard, N. Krause and
A. Alexakis, Angew. Chem., 2009, 121, 9085; Angew. Chem.,
Int. Ed., 2009, 48, 8923; (e) H. Jiang, N. Holub,
˜
M. W. Paixao, C. Tiberi, A. Falcicchio and K. A. Jørgensen,
Chem.–Eur. J., 2009, 15, 9638; (f) C. Chandler, P. Galzerano,
A. Michrowska and B. List, Angew. Chem., 2009, 121, 2012;
Angew. Chem., Int. Ed., 2009, 48, 1978; (g) C. Grondal,
M. Jeanty and D. Enders, Nat. Chem., 2010, 2, 167; (h)
B. Westermann, M. Ayaz and S. S. van Berkel, Angew.
Chem., 2010, 122, 858; Angew. Chem., Int. Ed., 2010, 49,
846; (i) N. T. Jui, E. C. Y. Lee and D. W. C. MacMillan, J.
Am. Chem. Soc., 2010, 132, 10015; (j) Ł. Albrecht, H. Jiang,
G. Dickmeiss, B. Gschwend, S. G. Hansen and
K. A. Jørgensen, J. Am. Chem. Soc., 2010, 132, 9188; (k)
(R)-Dichloroisoproterenol (3)8,24
White solid. 1H NMR (300 MHz, CDCl3): d ¼ 7.44 (d, 1H, J ¼ 1.88
Hz), 7.37 (d, 1H, J ¼ 8.26 Hz), 7.15 (dd, 1H, J ¼ 1.62 Hz, and 8.28
Hz), 4.57 (dd, 1H, J ¼ 3.61 Hz, and 9.01 Hz), 2.86 (dd, 1H, J ¼
3.64 Hz, and 12.12 Hz), 2.77 (sept, 1H, J ¼ 6.29 Hz), 2.54 (dd, 1H,
J ¼ 9.03, and 12.13 Hz), 1.04 (d, 6H, J ¼ 6.28 Hz). 13C-NMR (300
MHz, CDCl3): d ¼ 143.2, 132.4, 131.1, 130.2, 127.7, 125.1, 70.7,
54.3, 48.7, 23.1, 22.9. MS (EI) m/z: 230 (M–OH, 13%), 214 (M–Cl,
100). Chiral HPLC (Chiralpak IC, n-hexane–2-PrOH–ethanol-
amine 94.9 : 5 : 0.1, ow rate 0.5 mL minꢁ1, l ¼ 280 nm): tR 10.3
min (R), 11.1 min (S).
´
K. L. Jensen, P. T. Franke, C. Arroniz, S. Kobbelgaard and
K. A. Jørgensen, Chem.–Eur. J., 2010, 16, 1750; (l)
T. Urushima, D. Sakamoto, H. Ishikawa and Y. Hayashi,
Org. Lett., 2010, 12, 4588; (m) K. Weiß, S.-W. Wei and
S. B. Tsogoeva, Org. Biomol. Chem., 2011, 9, 3457; (n)
S.-W. Wei, K. M. Weiß and S. B. Tsogoeva, Synthesis, 2012,
44, 3441; (o) M. M. Ibrahim, D. Grau, F. Hampel and
S. B. Tsogoeva, Eur. J. Org. Chem., 2014, 1401.
Acknowledgements
We thank Dr Frank Hampel, Institute of Organic Chemistry I,
for the X-Ray structure determination. S. B. T. is grateful to the
Interdisciplinary Center for Molecular Materials (ICMM) and
Erlangen Catalysis Resource Center (ECRC) for research
support.
ˇ
5 (a) D. Enders, V. Terteryan and J. Palecek, Synthesis, 2008, 14,
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Notes and references
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A. Dondoni and A. Massi, Angew. Chem., Int. Ed., 2008, 47,
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7 A. Solladie-Cavallo and A. Diep-Vohuule, J. Org. Chem., 1995,
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8 S.-W. Wei, R. Messerer and S. B. Tsogoeva, Chem.–Eur. J.,
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2 Ł. Albrecht, H. Jiang and K. A. Jørgensen, Angew. Chem., Int.
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9 M. Dukes and L. H. Smith, J. Med. Chem., 1971, 14, 326 and
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and M. R. M. Huttl, Angew. Chem., 2007, 119, 1590; Angew. 13 Y.-Q. Wen, R. Hertzberg, I. Gonzalez and C. Moberg, Chem.–
Chem., Int. Ed., 2007, 46, 1570; (e) C. Vaxelaire, P. Winter
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Eur. J., 2014, 20, 3806.
32800 | RSC Adv., 2014, 4, 32796–32801
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