Gary M. Noonan et al.
FULL PAPERS
A
Pringle, A. M. Ward, D. A. Zambrano-Williams, Dalton
Trans. 2005, 1079; c) B. Breit, E. Fuchs, Chem.
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Kamer, P. W. N. M. van Leeuwen, Organometallics
1995, 14, 34.
two steps, one isolation); [a]2D0: À22.2 (c 4.0, CDCl3, ee=
62%) [Lit.[16] À33.58 (c 1.15 CHCl3, pure R-enantiomer); IR:
nmax =3408, 2974, 2935, 2876, 1617, 1464, 1381, 1264, 1219,
1150, 1123, 1040 cmÀ1 1H NMR (400 MHz, CDCl3): d=
;
3.62–3.71 (m, 2H), 3.14–3.50 (m, 5H), 2.7–2.83 (m, 1H),
1.16 (t, J=7.0 Hz, 3H) 1.13 (d, J=7.0 Hz, 3H), 1.07 (t, J=
7.0 Hz, 3H); 13C NMR (400 MHz, CDCl3): d=175.6, 65.1,
41.8, 40.0, 37.5, 14.7, 14.3, 13.0; HR-MS (ES+): m/z=
182.1163 [M+Na]+, C8H17NO2Na requires 182.1157.
[4] Some recent tandem processes: a) P. S. Bꢇuerlein, I. A.
Gonzalez, J. J. M. Weemers, M. Lutz, A. L. Spek, D.
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Synth. Catal. 2007, 349, 1897; d) O. Abillard, B. Breit,
Adv. Synth. Catal. 2007, 349, 1891.
[5] Reviews on tandem processes: a) P. Eilbracht, L. Bꢇr-
facker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon,
C. L. Kranemann, T. Rische, R. Roggenbuck, A.
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Schmidt, Top. Organomet. Chem. 2006, 18, 65.
[6] M. Dieguez, O. Pamies, A. Ruiz, S. Castillon, C.
Claver, Chem. Eur. J. 2001, 7, 3086.
ACHTUNGTRENNUNG(12B) (alcohol derived from 9B): Yield: 105 mg (56%
over two steps, one isolation); [a]2D0: À12.2 (c 2.1, CDCl3,
ee=50%). IR: nmax =3422, 2967, 1617, 1444, 1371, 1210,
1
1137, 1028 cmÀ1; H NMR (400 MHz, MeOD): d=3.97–4.21
(m, 1H), 3.62 (dd, J=10.6, 7.4 Hz, 1H), 3.54 (m, 1H), 3.37
(dd, J=10.6, 6 Hz, 1H), 2.77–2.89 (m, 1H), 1.21–1.32 (m,
6H), 1.10–1–21 (m, 6H), 0.97 (d, J=6.8 Hz, 3H); 13C NMR
(400 MHz, CDCl3): d==174.4, 64.2, 47.1, 44.8, 37.8, 20.1,
20.0, 19.7, 19.5, 13.2; HR-MS (ES+): m/z=210.1464 [M+
Na]+, C10H21NO2Na requires 210.1470; anal. calcd. for
C10H21NO2: C 64.13, H 11.30, N 7.48; found: C 64.02, H
11.26, N 7.50.
[7] C. J. Cobley, K. Gardner, J. Klosin, C. Praquin, C. Hill,
G. T. Whiteker, A. Zanotti-Gerosa, J. L. Petersen,
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[8] C. J. Cobley, J. Klosin, C. Qin, G. T. Whiteker, Org.
Lett. 2004, 6, 3277.
Acknowledgements
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The authors thank Chirotech and EPSRC–Chemistry Innova-
tion Knowledge Transfer Network for funding (GMN), The
Royal Society of Edinburgh for the award of a “supports Re-
search” fellowship (MLC), and the European Union Interna-
tional Training Network (NANOHOST) for supporting the
collaboration between AP and MLC. Technical assistance
from Mrs. Melanya Smith, Mr. Peter Pogorzelec, and Mrs.
Carolyn Horsburgh is also gratefully acknowledged.
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1054
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Adv. Synth. Catal. 2010, 352, 1047 – 1054