b = 99.4840(10)u, V = 878.20(14) A , Z = 2, Dc = 1.238 Mg m23; in the
final least-square refinement cycles on F2, the model converged to R1 =
0.0462, wR2 = 0.0834 for 3567 reflections, CCDC 630581. Crystal data
for 2b (recrystallized from CHCl3–hexane): orthorhombic, space group
3
˚
Sports, Science and Technology (MEXT) of the Japanese
Government.
˚
P212121, a = 10.1985(5), b = 12.5024(6), c = 21.8216(10) A, V =
Notes and references
2782.4(2) A , Z = 4, Dc = 1.267 Mg m23; in the final least-square
3
˚
refinement cycles on F2, the model converged to R1 = 0.0443, wR2
=
1 M. Sakamoto, A. Unosawa, S. Kobaru, A. Saito, T. Mino and T. Fujita,
Angew. Chem., Int. Ed., 2005, 44, 5523–5526.
2 M. Sakamoto, T. Iwamoto, N. Nono, M. Ando, W. Arai, T. Mino and
T. Fujita, J. Org. Chem., 2003, 68, 942–946; M. Sakamoto, S. Kobaru,
T. Mino and T. Fujita, Chem. Commun., 2004, 1002–1003.
3 J. Jacques, A. Collet and S. H. Wilen, in Enantiomers, Racemates, and
Resolutions, Krieger Publishing, Malabar, FL, 1994, 369–377; H. Nohira
and K. Sakai, in Enantiomer Separation, ed. F. Toda, Kluwer Academic
Publishers, Netherlands, 2004, pp. 165–191; K. M. J. Brands and
A. J. Davies, Chem. Rev., 2006, 106, 2711–2733.
4 R. E. Pincock, R. R. Perkins, A. S. Ma and K. R. Wilson, Science, 1971,
174, 1018–1020; D. K. Kondepudi, J. Laudadio and K. Asakura, J. Am.
Chem. Soc., 1999, 121, 1448–1449; M. Sakamoto, T. Utsumi, M. Ando,
M. Saeki, T. Mino, T. Fujita, A. Katoh, T. Nishio and C. Kashima,
Angew. Chem., Int. Ed., 2003, 42, 4360–4363.
0.1204 for 6395 reflections, CCDC 630582. For crystallographic data in
CIF or other electronic format see DOI: 10.1039/b617888j.
6 Photochemical cycloaddition of 9-cyanoanthracene and naphthalene has
been reported: A. Albini, E. Fasani and D. Faiardi, J. Org. Chem., 1987,
52, 155–157.
7 We reported the rate of enantiomerization of axially chiral 1-naphtha-
mide, which was suppressed in a protic solvent rather than an aprotic
solvent, and was explainable in terms of hydrogen bonding, see ref. 1.
8 A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy,
J. H. Pink, N. Westlund and S. A. Yasin, Tetrahedron, 1998, 54,
13277–13294.
9 For recent reviews for stereoselective photoreactions, see: S. S. L. Everritt
and Y. Inoue, in Organic Molecular Photochemistry, ed. V. Ramamurthy,
K. S. Schanze, Marcel Dekker, New York, 1999, vol. 3, pp. 71–130;
Y. Inoue, in Chiral Photochemistry, ed. Y. Inoue and V. Ramamurthy,
Marcel Dekker, New York, 2004, pp. 129–177; N. Hoffmann and J.-P.
Pete, in Chiral Photochemistry, ed. Y. Inoue and V. Ramamurthy, Marcel
Dekker, New York, 2004, pp. 179–233; B. L. Feringa and R. Van Delden,
Angew. Chem., Int. Ed., 1999, 38, 3419–3438; M. Sakamoto, in Chiral
Photochemistry, ed. Y. Inoue and V. Ramamurthy, Marcel Dekker, New
York, 2004, pp. 415–461; A. G. Griesbeck and U. J. Meierhenrich,
Angew. Chem., Int. Ed., 2002, 41, 3147–3154.
5 Crystal data: for (S,aR)-1a (recrystallized from CHCl3–hexane):
monoclinic, space group P21, a = 11.0267(17), b = 6.9804(11), c =
3
˚
˚
11.2114(17) A, b = 116.392(2)u, V = 773.0(2) A , Z = 2, Dc
=
1.346 Mg m23; in the final least-square refinement cycles on F2, the model
converged to R1 = 0.0352, wR2 = 0.0884 for 4315 reflections, CCDC
630580. Crystal data for (S,aR)-1b (recrystallized from CHCl3–hexane):
monoclinic, space group P21, a = 7.6617(7), b = 12.7932(12), c =
˚
9.0838(8) A,
1634 | Chem. Commun., 2007, 1632–1634
This journal is ß The Royal Society of Chemistry 2007