A novel catalytic enantioselective tandem transetherification-intramolecular hetero Diels-Alder reaction of methyl (E)-4-methoxy-2-oxo-3-butenoate with δ,ε-unsaturated alcohols

Tetrahedron Letters

Volumn 43, Issue 51, 2002, Pages 9397-9400

  Wada, Eiji ^a   Koga, Hidetaka ^a   Kumaran, Govindaraj ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

1 oxa 1,3 butadiene; Chiral Lewis acid catalyst; Enantioselective reaction; Intramolecular hetero Diels Alder reaction; Molecular sieves; Tandem reaction; Transetherification

Indexed keywords

ALCOHOL DERIVATIVE; COPPER DERIVATIVE; LIGAND; METHYL 4 METHOXY 2 OXO 3 BUTENOATE; METHYL GROUP; OXAZOLINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; TANDEM TRANSETHERIFICATION;

BETULACEAE;

EID: 0037121614     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02320-1     Document Type: Article

References (37)

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25. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
26. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
27. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
28. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
29. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
30. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
31. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
32. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
33. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
34. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
35. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
36. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.
37. For the role of 4 Å MS in catalytic asymmetric reactions, see: (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345; (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820; (c) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644; (d) Posner, G. H.; Dai, H.; Bull, D S.; Lee, J.-K.; Eydoux, F.; Ishihara, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671-676; (e) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281-282; (f) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, J. Mol. Catal. A 1998, 132, 165-169; (g) Mikami, K.; Terada, M.; Matsumoto, Y.; Tanaka, M.; Nakamura, Y. Microporous and Mesoporous Mater. 1998, 21, 461-466; (h) Gotherf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488; (i) Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. Tetrahedron 1998, 54, 15721-15730; (j) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3213-3216; (k) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667; (l) Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organometallic Chem. 2000, 603, 6-12; (m) Moharram, S. M.; Hirai, Go.; Koyama, K.; Oguri, H.; Hirama, M. Tetrahedron Lett. 2000, 41, 6669-6673.