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7 For the preparation of sulfamides 1a–1f, see supporting
informationw.
8 For reviews of organocatalytic conjugate addition, see:
(a) D. Almasi, D. A. Alonso and C. Najera, Tetrahedron: Asym-
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9 For selected publications on asymmetric conjugate addition of
aldehydes and ketones to nitroolefins, see: (a) P. Garcıa-Garcıa,
A. Ladepeche, R. Halder and B. List, Angew. Chem., Int. Ed., 2008,
47, 4719–4721; (b) Y. Hayashi, T. Itoh, M. Ohkubo and
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Scheme 2 Proposed catalytic mechanism.
aldehydes to nitroolefins. Base additives greatly accelerate the
reaction. The results suggest that the sulfamide is another
useful catalaphore for double hydrogen-bonding activation in
organocatalysis.
Financial support of this research by the National Natural
Science Foundation of China (No. 20772160), the Ministry of
Education (NCET project) and the Guangzhou Bureau of
Science and Technology is gratefully acknowledged.
Notes and references
1 For recent reviews of hydrogen-bonding activation, see:
(a) S. J. Connon, Chem.–Eur. J., 2006, 12, 5418–5427;
(b) M. S. Taylor and E. N. Jacobsen, Angew. Chem., Int. Ed.,
2006, 45, 1520–1543; (c) X. H. Yu and W. Wang, Chem.–Asian J.,
2008, 3, 516–532; (d) A. G. Doyle and E. N. Jacobsen, Chem. Rev.,
2007, 107, 5713–5743; (e) T. Akiyama, J. Itoh and K. Fuchibe,
Adv. Synth. Catal., 2006, 348, 999–1010.
2 For recent reviews of asymmetric organocatalysis, see:
(a) A. Dondoni and A. Massi, Angew. Chem., Int. Ed., 2008, 47,
4638–4660; (b) P. I. Dalko, Enantioselective Organocatalysis:
Reactions and Experimental Procedures, Wiley-VCH Verlag
10 See supporting information for the details of solvent effectsw.
11 IR (thin film) n/cmÀ1: 3035 (w), 1561 (s), 1496 (m), 1455 (m), 1365 (m),
1282 (m), 738 (m), 700 (s). Elemental analysis: C 64.58, H 6.27,
N 9.21%.
12 M. E. Carter, J. L. Nash, Jr, J. W. Drueke, Jr, J. W. Schwietert and
G. B. Butler, J. Polym. Sci., Polym. Chem. Ed., 1978, 16, 937–959.
ꢀc
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