J.-H. Lee et al. / Tetrahedron 63 (2007) 7906–7915
7915
(k) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int.
Ed. 1996, 35, 2708; (l) Wirth, T. Angew. Chem., Int. Ed. 1997,
ꢀ
36, 225; (m) Cativiela, C.; Dıaz-de-Villegas, M. D.
Tetrahedron: Asymmetry 1998, 9, 3517; (n) Cativiela, C.;
ꢀ
Dıaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11,
645; (o) Burk, M. J. Acc. Chem. Res. 2000, 33, 363; (p)
Chem., Int. Ed. 2003, 42, 579; (e) Ooi, T.; Kameda, M.;
Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139; (f)
Hashimoto, T.; Maruoka, K. Tetrahedron Lett. 2003, 44,
3313; (g) Hashimoto, T.; Tanaka, Y.; Maruoka, K.
Tetrahedron: Asymmetry 2003, 14, 1599; (h) Ooi, T.; Kubota,
Y.; Maruoka, K. Synlett 2003, 1931; (i) Maruoka, K. P. Jpn.
Acad. B–Phys. 2003, 79, 181; (j) Ooi, T.; Maruoka, K.
J. Synth. Org. Chem. Jpn. 2003, 61, 1195; Arai et al. also
reported the L-tartrate-derived chiral spiro ammonium salts
and their application to Michael reaction of 1, see: (k) Arai,
S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535.
12. Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa,
K. Angew. Chem., Int. Ed. 2002, 41, 2832.
ꢀ
ꢀ
Abellan, T.; Chinchilla, R.; Galindo, N.; Guillena, G.; Najera,
C.; Sansano, J. M. Eur. J. Org. Chem. 2000, 2689;
(q) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40,
40; (r) Yet, L. Angew. Chem., Int. Ed. 2001, 40, 875; (s) Rossen,
K. Angew. Chem., Int. Ed. 2001, 40, 4611; (t) Ma, J.-A. Angew.
Chem., Int. Ed. 2003, 42, 4290.
4. (a) Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis,
3rd ed.; VCH: Weinheim, 1993; (b) Starks, C. M.; Liotta,
C. L.; Halpern, M. Phase-Transfer Catalysis; Chapman &
Hall: New York, NY, 1994; (c) Handbook of Phase-Transfer
Catalysis; Sasson, Y., Neumann, R., Eds.; Blackie Academic
& Professional: London, 1997; (d) Phase-Transfer Catalysis;
Halpern, M. E., Ed.; ACS Symposium Series 659; American
Chemical Society: Washington, DC, 1997; (e) Nelson, A.
Angew. Chem., Int. Ed. 1999, 38, 1583; (f) Shioiri, T.
Handbook of Phase-Transfer Catalysis; Sasson, Y., Neumann,
R., Eds.; Blackie Academic & Professional: London, 1997;
Chapter 14; (g) O’Donnell, M. J. Catalytic Asymmetric
Synthesis, 2nd ed.; Ojima, I., Ed.; Chemie: New York, NY,
2000; Chapter 10; (h) Shioiri, T.; Arai, S. Stimulating
Concepts in Chemistry; Vogtle, F., Stoddart, J. F., Shibasaki,
M., Eds.; Wiley-VCH: Weinheim, 2000; pp 123–143.
5. For excellent reviews: (a) O’Donnell, M. J. Aldrichimica Acta
2001, 34, 3; (b) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103,
3013; (c) O’Donnell, M. J. Acc. Chem. Res. 2004, 37, 506;
(d) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518;
(e) Ooi, T.; Maruoka, K. Acc. Chem. Res. 2004, 37, 526.
6. O’Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.
7. O’Donnell, M. J.; Delgado, F.; Pottorf, R. S. Tetrahedron 1999,
55, 6347.
8. (a) O’Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc.
1989, 111, 2353; (b) Lipkowitz, K. B.; Cavanaugh, M. W.;
Baker, B.; O’Donnell, M. J. J. Org. Chem. 1991, 56, 5181;
(c) O’Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron
1994, 50, 4507.
9. (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38,
8595; (b) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron
Lett. 1999, 40, 1385; (c) Lygo, B.; Crosby, J.; Lowdon, T. R.;
Wainwright, P. G. Tetrahedron 2001, 57, 2391; (d) Lygo, B.;
Crosby, J.; Peterson, J. A. Tetrahedron 2001, 57, 2403;
(e) Lygo, B.; Andrew, B. I.; Crosby, J.; Peterson, J. A.
Tetrahedron Lett. 2002, 43, 8015.
13. (a) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima,
T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539; (b)
Ohshima, T.; Gnanadesikan, V.; Shibuguchi, T.; Fukuta, Y.;
Nemoto, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 11206.
14. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino,
G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa,
K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992,
57, 2768; (b) Amberg, W.; Bennani, Y. L.; Chadha, R. K.;
Crispino, G. A.; David, W. D.; Hartung, J.; Jeong, K.-S.;
Ogino, Y.; Shibata, T.; Sharpless, K. B. J. Org. Chem. 1993,
58, 844; (c) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.;
Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993,
58, 3785.
15. Preliminary communications: (a) Jew, S.-s.; Jeong, B.-S.; Yoo,
M.-S.; Huh, H.; Park, H.-g. Chem. Commun. 2001, 1244; (b)
Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Park, M.-k.; Huh, H.;
Jew, S.-s. Tetrahedron Lett. 2001, 42, 4645; (c) Park, H.-g.;
Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-k.; Lee, Y.-J.;
Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036.
16. Baba, N.; Oda, J.; Kawakuchi, M. Agric. Biol. Chem. 1986, 50,
3113.
17. The modeling was done using the program SYBYL 6.5 from
Tripos Software Inc., Saint Louis, MI, USA.
18. In the course of this research, a similar work was reported by
ꢀ
another group. See: Chinchilla, R.; Mazon, P.; Najera, C.
ꢀ
Tetrahedron: Asymmetry 2002, 13, 927.
19. As of August 2006, the catalyst 41 can be purchased from
the Sigma–Aldrich Co. under the name of ‘O,O0-diallyl-N,N0-
(2,7-naphthalenediyldimethyl)bis(hydrocinchonidinium) dibro-
mide’ (product number: Fluka 06542).
20. For reports on the application of our polymeric PTCs to total
syntheses or other reactions, see: (a) Lee, J.-H.; Jeong, B.-S.;
Ku, J.-M.; Jew, S.-s.; Park, H.-g. J. Org. Chem. 2006, 71,
6690; (b) Jew, S.-s.; Lee, J.-H.; Jeong, B.-S.; Yoo, M.-S.;
Lim, M.-J.; Lee, Y.-J.; Lee, J.; Choi, S.-h.; Lee, K.; Lah,
M. S.; Park, H.-g. Angew. Chem., Int. Ed. 2005, 44, 1383; (c)
Danner, P.; Bauer, M.; Phukan, P.; Maier, M. E. Eur. J. Org.
Chem. 2005, 317; (d) Yu, H.; Takigawa, S.; Koshima, H.
Tetrahedron 2004, 60, 8405; (e) Kim, S.; Lee, J.; Lee, T.;
Park, H.-g.; Kim, D. Org. Lett. 2003, 5, 2703; (f) Matsushita,
M.; Yoshida, K.; Yamamoto, N.; Wirsching, P.; Lerner, R. A.;
Janda, K. D. Angew. Chem., Int. Ed. 2003, 42, 5984.
10. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997,
119, 12414; (b) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron
Lett. 1998, 39, 5347.
11. (a) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999,
121, 6519; (b) Maruoka, K. J. Fluorine Chem. 2001, 112, 95;
(c) Ooi, T.; Uematsu, Y.; Maruoka, K. Adv. Synth. Catal.
2002, 344, 288; (d) Ooi, T.; Tayama, E.; Maruoka, K. Angew.