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Volumn 70, Issue 4, 2005, Pages 1369-1375

Lipase-catalyzed resolution of (2R*,3S*)- and (2R*,3R*)-3-methyl-3-phenyl-2-aziridinemethanol at low temperatures and determination of the absolute configurations of the four stereoisomers

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; DERIVATIVES; ESTERS; METHANOL; PHENOLS; REACTION KINETICS; X RAY ANALYSIS;

EID: 13844306889     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048243n     Document Type: Article
Times cited : (28)

References (39)
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    • 33748605775 scopus 로고    scopus 로고
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    • note
    • Frequency calculation performed on optimized structures at the same level produced no imaginary frequencies.
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    • We have recently reported that lipase PS-C II is also usable at high temperature up to 120°C and that it is effectively applicable to a bulky substrate: Ema, T.; Kageyama, M.; Korenaga, T.; Sakai, T. Tetrahedron: Asymmetry 2003, 14, 3943-3947.
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    • For recent examples: (a) Itoh, T.; Kawai, K.; Hayase, S.; Ohara, H. Tetrahedron Lett. 2003, 44, 4081-4084. (b) Kurokawa, M.; Shindo, T.; Suzuki, M.; Nakajima, N.; Ishihara, K.; Sugai, T. Tetrahedron: Asymmetry 2003, 14, 1323-1333. (c) Murakami, M.; Kamaya, H.; Kaneko, C.; Sato, M. Tetrahedron: Asymmetry 2003, 14, 201-215. (d) de Gonzalo, G.; Brieva, R.; Sánchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2003, 68, 3333-3336.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1323-1333
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    • 0037449667 scopus 로고    scopus 로고
    • For recent examples: (a) Itoh, T.; Kawai, K.; Hayase, S.; Ohara, H. Tetrahedron Lett. 2003, 44, 4081-4084. (b) Kurokawa, M.; Shindo, T.; Suzuki, M.; Nakajima, N.; Ishihara, K.; Sugai, T. Tetrahedron: Asymmetry 2003, 14, 1323-1333. (c) Murakami, M.; Kamaya, H.; Kaneko, C.; Sato, M. Tetrahedron: Asymmetry 2003, 14, 201-215. (d) de Gonzalo, G.; Brieva, R.; Sánchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2003, 68, 3333-3336.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 201-215
    • Murakami, M.1    Kamaya, H.2    Kaneko, C.3    Sato, M.4
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    • 0037453619 scopus 로고    scopus 로고
    • For recent examples: (a) Itoh, T.; Kawai, K.; Hayase, S.; Ohara, H. Tetrahedron Lett. 2003, 44, 4081-4084. (b) Kurokawa, M.; Shindo, T.; Suzuki, M.; Nakajima, N.; Ishihara, K.; Sugai, T. Tetrahedron: Asymmetry 2003, 14, 1323-1333. (c) Murakami, M.; Kamaya, H.; Kaneko, C.; Sato, M. Tetrahedron: Asymmetry 2003, 14, 201-215. (d) de Gonzalo, G.; Brieva, R.; Sánchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2003, 68, 3333-3336.
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    • De Gonzalo, G.1    Brieva, R.2    Sánchez, V.M.3    Bayod, M.4    Gotor, V.5
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    • note
    • -3, R = 0.069 for 2615 observed reflections [I > 2.00σ(I)] and 329 variable parameters. All measurements were made on a Rigaku RAXIS-IV imaging plate area detector with Mo Kα radiation. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-255492.


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