Lipase-catalyzed kinetic resolution of cyclobutylmethanols and determination of absolute stereochemistry by X-ray analysis

Enantiomer

Volumn 2, Issue 2, 1997, Pages 127-131

  Nemoto, Hideo ^a   Miyata, Junji ^a   Fukumoto, Keiichiro ^a   Ehara, Hitoshi ^a   Harada, Nobuyuki ^a   Uekusa, Hidehiro ^b   Ohashi, Yuji ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Absolute stereochemistry; Benzocyclobutylmethanol; Chiral auxiliary; Cyclobutylmethanol; Kinetic resolution; Lipase; X ray crystallography

Indexed keywords

ALKANOL; CYCLOBUTANE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

CRYSTALLOGRAPHY; DRUG ISOLATION; ENANTIOMER; ENZYME ACTIVITY; EVAPORATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SHORT SURVEY; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030757290     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (29)

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15. This was a gift from Amano Pharmaceutical Co., Ltd.
16. 1H NMR (500 MHz) analysis of the MTPA ester of the alcohol obtained by hydrolysis (LiOH) of 7 (Scheme 3).
17. (a) Harada, N., Soutome, T., Murai, S. and Uda, H. (1993). Tetrahedron: Asymmetry, 4, 1755-1758.
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22. See also: (a) Toyota, S., Miyasaka, T. and Oki, M. (1993). Chem. Lett., 1571-1574.
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24. (a) Harada, N., Nehira, T., Soutome, T., Hiyoshi, N. and Kido, F. (1996). Enantiomer, 1, 35-39.
25. (b) Harada, N., Koumura, N. and Robillard, M. Enantiomer, in press.
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27. See also: (d) Toyota, S., Yasutomi, A. and Oki, M. (1995). Tetrahedron Lett., 36, 6297-6300.
28. 3) δ 0.97 (3 H, s), 1.20 (3 H, s), 1.37-1.47 (2 H, m), 1.92-1.94 (3 H, m), 2.17 (1 H, br s), 2.48 (1 H, br d, J = 14.2 Hz), 2.87 (1 H, dd, J = 14.3, 2.2 Hz), 3.34 (1 H, dd, J = 14.3, 5.3 Hz), 3.40 (1 H, d, J = 13.9 Hz), 3.43 (1 H, d, J = 13.9 Hz), 3.79 (3 H, s), 3.81 (1 H, dddd, J = 7.5, 7.4, 5.3, 2.2 Hz), 4.06 (1 H, dd, J = 8.2, 5.3 Hz), 4.46 (1 H, dd, J = 12.6, 7.5 Hz), 4.49 (1 H, dd, J = 12.6, 7.4 Hz), 6.72 (1 H, d, J = 2.0 Hz), 6.77 (1 H, dd, J = 8.0, 2.0 Hz), 7.04 (1 H, d, J = 8.0 Hz), 7.53 (1 H, s), 8.02 (1 H, s).
29. w = 0.1747 for 2110 reflections [I > 2σ(I)].