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and 8, respectively. Alcohol 19 was analyzed using a
Chiralcel OB-H column; for ( )-19: tR 12.5 (S) and 16.9
(R) min, Rs 6.9 (hexane/propan-2-ol 90:10, 0.5 mL/min).
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2.6 (hexane/propan-2-ol 97:3, 0.8 mL/min). Acetate 12
was analyzed using a Chiralcel OB-H column; for
( )-12: tR 10.9 (R) and 11.8 (S) min, Rs 1.5 (hexane/
propan-2-ol 92:8, 0.5 mL/min). Acetates 22 and 23 were
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sponding alcohols 20 and 21.
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ꢀ
15. Garcıa-Urdiales, E.; Rebolledo, F.; Gotor, V. Adv. Synth.
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16. In a kinetic study, we had demonstrated that tert-
butylmethyl ether is the solvent in which CALB exhibits
The absolute configuration of the remaining amines and
alcohols obtained in the enzymatic processes were
determined by comparison of the sign of their optical
rotations with those reported. Consequently, absolute
configuration for the amides and esters was established.
ꢀ
a higher catalytic activity: Garcıa-Alles, L. F.; Gotor, V.
Biotechnol. Bioeng. 1998, 59, 684–694.
ꢁ
17. For the resolution of ( )-2, the use of 4 A molecular sieves
was not necessary. In these conditions, although anhy-
drous ButOMe was used, a side CALB-catalyzed hydro-
lysis of the acyl donor 12 took place. Thus, the resulting
(R)-1-phenylethanol arose from aminolysis and hydrolysis
of ( )-12. For this reason, enantiomeric ratio for the acyl
donor was not determined. Nevertheless, the high ee
(92%) obtained for the alcohol reveals that the (S)-
enantiomer of the acyl donor (S)-12 was almost
unreacted.
Acknowledgements
We thank Novo Nordisk Co. for the generous gift of the
CALB. This work has been supported by grants from
MCYT (Spain; Project PPQ-2001-2683) and the Prin-
cipado de Asturias (Spain; Project GE-EXP01-03).
J.G.-S. thanks the Spanish MEC for a predoctoral
fellowship.
18. Balkenhohl, F.; Ditrich, K.; Hauer, B.; Ladner, W. J.
prakt. Chem. 1997, 339, 381–384.
19. ( )-1-Phenylethanol was previously resolved with CALB
using S-ethyl thiooctanoate (E > 200): Frykman, H.;
€
Ohrner, N.; Norin, T.; Hult, K. Tetrahedron Lett. 1993,
34, 1367–1370.
References and notes
20. ( )-trans-2-Phenylcyclopentanol was previously resolved
(E > 100) with a lipase derived from Pseudomonas sp
(SAM II) under similar reaction conditions: Seemayer, R.;
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21. Enzyme-catalyzed kinetic resolution of ( )-21 has not
been reported. Synthesis of ( )-21 was carried out from
( )-20 by Mitsunobu reaction with p-nitrobenzoic acid
and subsequent hydrolysis of the resulting ( )-cis-2-
phenylcyclopentyl p-nitrobenzoate.
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