C. M. R. Ribeiro et al. / Tetrahedron Letters 42 (2001) 6477–6479
6479
Acknowledgements
9. Keukeleire, D. D.; Saeyens, W. Synth. Commun. 1996, 26,
4397–4402.
10. Typical procedure: Racemic ester 1 (1 mmol) was com-
bined with pH 7 or 8 (Table 1) phosphate buffer (10 ml)
and the enzyme (units; Table 1) at room temperature.
The reaction was maintained in an ultrasound bath,
during the time specified in Table 1. The pH was main-
CAPES and PROPP/UFF.
References
tained constant by continuous addition of 0.25
M
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aqueous NaOH. After the conversion (Table 1) the reac-
tion mixture was diluted with aqueous NaHCO3 and
extracted three times with ether, the combined organic
solution was dried (MgSO4) and concentrated to afford
(R)-1 (the % yield and e.e. are presented in Table 1). The
combined aqueous solution was acidified to pH 1 with
3N HCl and extracted three times with ether. The
extracts were dried (MgSO4) and concentrated to afford
acid (S)-2 (the % yield and e.e. are presented in Table 1).
Ethyl 3-hydroxy-3-phenylpropanoate 1:2 Colorless oil. H
1
NMR (300 MHz, CDCl3), l (ppm): 1.27 (3H, t, J=7.2
Hz); 2.70 (1H, dd, J=16.4 Hz and 4.8 Hz); 2.77 (1H, dd,
J=16.4 Hz and 8.4 Hz); 3.27 (sl; -OH); 4.18 (2H, q,
J=7.2 Hz); 5.13 (1H, dd, J=8.4 and 4.8 Hz); 7.26–7.40
(5H, m). 13C NMR (75 MHz, CDCl3), l (ppm): 14.0;
43.2; 60.8; 70.2; 125.6; 127.7; 128.4; 142.4; 172.3.
3-Hydroxy-3-phenylpropanoic acid 2:2 mp=115°C. 1H
NMR (300 MHz, CDCl3), l (ppm): 2.78 (1H, dd, J=16.5
Hz and 3.9 Hz); 2.86 (1H, dd, J=16.5 and 9.0 Hz); 3.80
(sl; -OH); 5.17 (1H, dd, J=9.0 and 3.9 Hz); 7.28–7.41
(5H, m). 13C NMR (75 MHz, CDCl3), l (ppm): 44.0;
70.3; 125.9; 127.4; 128.4; 144.8; 172.2.
11. Ethyl 3-cyclohexyl-3-hydroxy-3-phenylpropanoate: Col-
orless oil; 1H NMR (300 MHz, CDCl3), l (ppm): 0.97–
1.77 (12H, m), 1.03 (3H, t, J=7.2 Hz), 2.85 (1H, d,
J=15.6 Hz), 3.01 (1H, d, J=15.6 Hz), 3.96 (2H, q,
J=7.2 Hz), 7.18–7.49 (5H, m); 13C NMR (75 MHz,
CDCl3), l (ppm): 13.7, 26.2, 26.9, 42.2, 42.2, 48.6, 60.4,
77.1, 125.7, 126.5, 127.6, 144.9, 173.4. 3-Cyclohexyl-3-
hydroxy-3-phenylpropanoic acid: mp 174°C; 1H NMR
(300 MHz, CDCl3), l (ppm): 0.88–1.74 (11H, m), 2.90
(1H, d, J=15.9 Hz), 3.06 (1H, d, J=15.9 Hz), 7.20–7.36
(5H, m); 13C NMR (75 MHz, CDCl3), l (ppm): 26.1,
26.3, 26.4, 26.7, 26.9, 41.5, 48.7, 77.0, 125.5, 126.8, 127.8,
144.3, 177.3.
5. Ribeiro, C. M. R.; Passaroto, E. N.; Brenelli, E. C. S. J.
Braz. Chem. Soc., in press.
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8. Ultrasound Bath, Cole Parmer Instrument (UL452E, 47
Hz).