˚
space group P21, a 5 11.3720(8), b 5 9.4378(7), c 5 13.8177(10) A,
In the case of the combination of 2 and (1R, 2R)-3, on the other
hand, small guest molecules can be trapped in a cavity by a
hydrogen bond, however, the large size cavity cannot recognize the
stereochemistry of the guest molecule. Hence, the enantiomeric
selectivity may decrease for the smaller guest molecules. Thus,
enantioselectivity of the guest alcohol depends on the structure of
the dicarboxylic acid. This means that we can design a host
structure that is suitable for a guest molecule by changing the
combination of its component molecules.
b 5 97.694(2)u, U 5 1469.66(18) A , Z 5 2, Dc 5 1.2347(2) g cm23, m(Mo
3
˚
Ka)
5
0.085 mm21
,
10974 reflections measured, 6872 unique
(Rint 5 0.0186), finalR(F2) 5 0.0430 using 5469 reflections with I .
2.0s(I), R(all data) 5 0.0531, T 5 293 K. CCDC 267538. As the crystals
contain only non-heavy atoms, the Flack parameters for both absolute
b504164c/ for crystallographic data in CIF or other electronic format.
1 J. L. Atwood, J. E. D. Davis, D. D. MacNicol and F. Vogtle,
Comprehensive Supramolecular Chemistry, vol 6 (Solid-state
Supramolecular Chemistry-Crystal Engineering), Elsevier, Oxford, 1996.
2 (a) M. J. Zaworotko, Angew. Chem. Int. Ed., 2000, 39, 3052; (b) D. Cheng,
M. A. Khan and R. P. Houser, Inorg. Chem., 2001, 40, 6858; (c) Z.-Y. Fu,
X.-T. Wu, J.-C. Dai, L.-M. Wu, C.-P. Cui and S.-M. Hu, Chem.
Commun., 2001, 1856; (d) S. W. Keller, Angew. Chem. Int. Ed., 1997, 36,
247; (e) S. W. Keller and S. Lopez, J. Am. Chem. Soc., 1999, 121, 6306; (f)
M. O’Keeffe, M. Eddaoudi, H. Li, T. Reinke and O. M. Yaghi, J. Solid.
State Chem., 2000, 152, 3; (g) H. Li, M. Eddaoudi, M. O’Keeffe and
O. M. Yaghi, Nature, 1999, 402, 276; (h) L. R. MacGillivray,
R. H. Groeneman and J. L. Atwood, J. Am. Chem. Soc., 1998, 120,
2676; (i) R. Robson, J. Chem. Soc., Dalton Trans., 2000, 3375; (j)
B. F. Abrahams, P. A. Jackson and R. Robson, Angew. Chem. Int. Ed.,
1998, 37, 2656; (k) K. Biradha, Y. Hongo and M. Fujita, Angew. Chem.,
Int, Ed., 2000, 39, 3843; (l) M. J. Zaworotko, Chem. Commun, 2001, 1.
3 (a) A. Stein, S. W. Keller and T. E. Mallouk, Science, 1993, 259, 1558; (b)
M. Eddaudoi, H. L. Li and O. M. Yaghi, J. Am. Chem. Soc., 2000, 122,
1391; (c) J. Jim, B. Chen, T. M. Reineke, H. Li, M. Eddaouddi,
D. B. Moler, M. O’Keeffe and O. M. Yaghi, J. Am. Chem. Soc., 2001,
123, 8339; (d) S. Noro, S. Kitagawa, M. Kondo and K. Seki, Angew.
Chem. Int. Ed., 2000, 39, 2082; (e) S. Noro, R. Kitaura, M. Kondo,
S. Kitagawa, T. Ishii, H. Matsuzaka and M. Yamashita, J. Am. Chem.
Soc., 2002, 124, 2568; (f) K. Seki, Chem. Commun., 2001, 1496.
4 (a) J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Reactions, and
Resolutions, Krieger Publishing Company, Malabar, FL, 1994; (b)
L. M. Pasteur, C. R. Acad. Sci., 1853, 37, 162; (c) P. Newman, Optical
Resolution Procedures for Chemical Compounds, Optical Resolution
Information Center, New York, 1981.
In conclusion, a two-component host system consisting of
carboxylic acid and amine derivatives was successfully created with
high enantioselectivity for secondary alkyl alcohols. Although only
the amine molecule has chirality, the supramolecular host
possesses two kinds of chirality by chirality transfer. The host
system is versatile as the optical resolution of guest molecule can be
tuned by the combination of the host component molecules. It is
expected that this type of host system can be used for a variety of
chiral recognition and asymmetric reactions.
Yoshitane Imai,a Tomohiro Satoa and Reiko Kuroda*ab
aJST ERATO-SORST Kuroda Chiromorphology Team, 4-7-6, Komaba,
Meguro-ku, Tokyo, 153-0041, Japan
bDepartment of Life Sciences, Graduate School of Arts and Sciences,
The University of Tokyo, Komaba, Meguro-ku, Tokyo, 153-8902,
Japan. E-mail: ckuroda@mail.ecc.u-tokyo.ac.jp
Notes and references
{ Crystallographic data of I: C14H18N2?C14H8O4?2(C2H5OH), M 5 546.64,
orthorhombic, space group P212121, a 5 9.7328(7), b 5 13.7878(9),
3
c 5 22.0639(14) A, U 5 2960.8(3) A , Z 5 4, Dc 5 1.2263(1) g cm23, m(Mo
Ka)
˚
˚
5 , 22219 reflections measured, 7357 unique
0.085 mm21
(Rint 5 0.0402), finalR(F2) 5 0.0464 using 4670 reflections with I .
2.0s(I), R(all data) 5 0.0726, T 5 293 K. CCDC 267537. Crystallographic
data of II: C14H18N2?C14H8O4?C4H10O?H2O, M 5 546.40, monoclinic,
5 C. Kassai, Z. Juvancz, J. Balint, E. Fogassy and D. Kozma, Tetrahedron,
2000, 56, 8355.
This journal is ß The Royal Society of Chemistry 2005
Chem. Commun., 2005, 3289–3291 | 3291