Chiral ligand controlled enantioselective opening of oxirane and oxetane

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2483-2484

  Mizuno, Masashi ^b   Kanai, Motomu ^a   Iida, Akira ^b   Tomioka, Kiyoshi ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE; LIGAND; OXETANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0039169610     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00312-6     Document Type: Article

References (18)

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3. 2. Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1992, 114, 8732-8733; Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527-2533, and references cited therein.
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6. 3. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643-1646; Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220; Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179-1180; Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc. Chem. Commun. 1994, 2699-2700; Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768-2769; Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81-84; Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898; Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
7. 3. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643-1646; Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220; Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179-1180; Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc. Chem. Commun. 1994, 2699-2700; Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768-2769; Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81-84; Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898; Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
8. 3. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643-1646; Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220; Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179-1180; Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc. Chem. Commun. 1994, 2699-2700; Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768-2769; Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81-84; Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898; Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
9. 3. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643-1646; Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220; Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179-1180; Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc. Chem. Commun. 1994, 2699-2700; Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768-2769; Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81-84; Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898; Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
10. 3. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643-1646; Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220; Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179-1180; Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc. Chem. Commun. 1994, 2699-2700; Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768-2769; Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81-84; Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898; Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
11. 3. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643-1646; Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220; Paterson, I.; Berrisford, D. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179-1180; Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc. Chem. Commun. 1994, 2699-2700; Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768-2769; Mischitz, M.; Faber, K. Tetrahedron Lett. 1994, 35, 81-84; Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898; Hodgson, D. M.; Wisedale, R. Tetrahedron: Asymmetry 1996, 7, 1275-1276.
12. 4. Chiral heterocuprates have been shown to open 2 giving the corresponding alcohol in at most 3.6% ee. Davies, S. G.; Wollowitz, S. Tetrahedron Lett. 1980, 21, 4175-4178.
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16. 3 used.
17. 6
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