726
E. García-Urdiales et al. / Tetrahedron: Asymmetry 10 (1999) 721–726
to yield O-benzoyl-1, which was purified by column chromatography (CH Cl :hexane 1:1 as eluent).
2
2
i
Chiral HPLC analysis (Chiralcel-OD, hexane:Pr OH 95:5, 0.4 mL/min): (R)-O-benzoyl-1, t 20.2 min;
R
(
ꢀ)-O-benzoyl-1, two peaks, t 18.1 and 20.2 min; Rs 2.5.
R
3.9. Determination of the ee of 2
A solution of 2 (0.36 mmol) in THF (1.5 mL) was treated with TBDPSCl (0.73 mmol) and imidazole
(1.46 mmol). When the reaction was finished (12 h, rt), the solvent was evaporated and AcOEt was added
to the residue. The organic solution was washed with 2 N HCl and water, dried and then evaporated to
yield O-TBDPS-2, which was purified by column chromatography (AcOEt:hexane 1:1 as eluent). Chiral
i
HPLC analysis (Chiralcel-OD, hexane:Pr OH 95:5, 0.8 mL/min): (S)-O-TBDPS-2, t 28.5 min; (ꢀ)-O-
R
TBDPS-2, two peaks, t 24.8 and 28.2 min; Rs 2.1.
R
Acknowledgements
We are grateful to the CICYT (Project BIO 98-0770) for financial support, to Novo Nordisk Co. for
the generous gift of the CA lipase, and E. G.-U. thanks the Ministerio de Educación y Ciencia for a
predoctoral fellowship.
References
1. (a) García, M. J.; Rebolledo, F.; Gotor, V. Tetrahedron Lett. 1993, 34, 6141–6142. (b) Sánchez, V.; Rebolledo, F.; Gotor,
V. Synlett 1994, 529–530. (c) Puertas, S.; Rebolledo, F.; Gotor, V. Tetrahedron 1995, 51, 1495–1502.
2. (a) Zoete, M. C.; Kock-van Dalen, A. C.; Rantwijk, F.; Sheldon, R. A. J. Chem. Soc., Chem. Commun. 1993, 1831–1832.
(
b) Zoete, M. C.; Ouwehand, A. A.; Rantwijk, F.; Sheldon, R. A. Recl. Trev. Chim. Pays Bas 1995, 114, 171–174. (c)
Puertas, S.; Rebolledo, F.; Gotor, V. J. Org. Chem. 1996, 61, 6024–6027.
3. (a) Pandey, G.; Chakrabarti, D. Tetrahedron Lett. 1996, 37, 2285–2288. (b) Farrant, E.; Mann, J. J. Chem. Soc., Perkin
Trans. 1 1997, 1083–1084.
4
5
6
. Gmeiner, P.; Orecher, F.; Thomas, Ch.; Weber, K. Tetrahedron Lett. 1995, 36, 381–382.
. Fedij, V.; Lenoir III, E. A.; Suto, M. J.; Zeller, J. R.; Wemple, J. Tetrahedron: Asymmetry 1994, 5, 1131–1134.
. (a) Naylor, A.; Judd, D. B.; Scopes, D. I. C.; Hayes, A. G.; Birch, P. J. J. Med. Chem. 1994, 37, 2138–2144. (b) Gottschlich,
R.; Ackermann, K. A.; Barber, A.; Bartoszyk, G. D.; Greiner, H. E. Bioorg. Med. Chem. Lett. 1994, 4, 677–682. (c)
Uchiyama, M. PCT Int. Appl. WO 94 18,165 (Cl. C07D207/12) 18 August 1994, CAS 1995, 122, 314448g. (d) Ito, F.
PCT Int. Appl. WO 96 06,078 (Cl. C07D207/12) 29 February 1996, CAS 1996, 125, 86487y.
. Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247–2248.
. See for example: (a) Terradas, F.; Teston-Henry, M.; Fitzpatrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115,
7
8
390–396. (b) Claon, P. A.; Akoh, C. C. Enzyme Microb. Technol. 1994, 16, 835–838.
9. Chen, Ch.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294–7299.
1
1
1
0. Zhou, B.-N.; Gopalan, A. S.; Van Middlesworth, F.; Shieh, W. R.; Sih, C. J. J. Am. Chem. Soc. 1983, 105, 5925–5926.
1. Zhang, L.-H.; Kauffman, G. S.; Pesti, J. A.; Yin, J. J. Org. Chem. 1997, 62, 6918–6920.
2. (a) For the synthesis of pyrrolidin-3-ol see: Flanagan, D. M.; Joullie’, M. M. Heterocycles 1987, 26, 2247–2265. (b) For
the synthesis of 5-(chloromethyl)-1,3-oxazolidin-2-one see: Danielmeier, K.; Steckhan, E. Tetrahedron: Asymmetry 1995,
6, 1181–1190.