W. Li et al. / Tetrahedron Letters 47 (2006) 3453–3457
3457
O
TMSN : (b) Martinez, L. E.; Leighton, J. L.; Carsten, D.
3
O
OH
H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897;
Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem.
1997, 62, 4197; Thiols: (c) Wu, M.; Jacobsen, E. N. J. Org.
Chem. 1998, 63, 5252; Phenols: (d) Ready, J. M.; Jacobsen,
E. N. J. Am. Chem. Soc. 1999, 121, 6086; ArSeH: (e) Yang,
M.; Zhu, C.; Yuan, F.; Huang, Y.; Pan, Y. Org. Lett. 2005,
7, 1927; HCl: (f) Thakur, S. S.; Li, W.; Kim, S. J.; Kim,
O
(
Cl
n-Pr
Cl
(
±)
n-Pr
OH
S)- 76.7 % ee
(A)
(
S,S) Cat. II-1-d, TBME, 0-4 ºC, 4h
O
O
(S,S) Cat. II-1-d
mol %
K PO , rt
2
n-Pr
O
3
4
overnight, TBME
2
G.-J. Tetrahedron Lett. 2005, 46, 2263; NH Boc: (g)
(
R) - 98.9% ee
O
Glycidyl butyrate (GB)
Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melch-
iorre, P.; Sambri, L. Org. Lett. 2004, 6, 3973; Bartoli, G.;
Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.;
Sambri, L. Org. Lett. 2004, 6, 2173.
Scheme 4.
2
. Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Shai-
bani, R. Tetrahedron 2004, 60, 6105, and references cited
therein; Bukowska, A.; Bukowski, W.; Leszczak, B. M. J.
Chem. Technol. Biotechnol. 1999, 74, 1145; Baum, K.;
Berkowitz, P. T.; Grakauskas, V.; Archibald, T. G. J. Org.
Chem. 1983, 48, 2953; Mirkhani, V.; Tangestaninejada, S.;
Yadollahib, B.; Alipanaha, L. Tetrahedron 2003, 59, 8213;
Junzo, O.; Shinjiro, M. Synthesis 1986, 12, 1019; Khalafi-
Nezhad, A.; Soltani Rad, M. N.; Khoshnood, A. Synthesis
of base and catalyst afforded glycidyl butyrate in high
9
1
8.9% ee and 40% yield. In the absence of catalyst II-
-d, the reaction proceeded slowly and formed racemic
mixture. The role of the catalyst II-1-d for asymmetric
cyclization may be understood by a similar report of
8
Takeichi et al.
(
R)-Glycidyl butyrate is a very important compound
2
003, 16, 2552.
and has been used to introduce a stereogenic center in
9
3. Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J.
F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773, and
references cited therein.
the synthesis of Linezolid, which is currently marketed
for the treatment of multidrug resistant Gram-positive
infections such as nosocomial, community-acquired
pneumonia, and skin infections.
4
. (a) Shin, C. K.; Kim, S. J.; Kim, G.-J. Tetrahedron Lett.
004, 45, 7429; (b) Thakur, S. S.; Li, W.; Shin, C. K.; Kim,
G.-J. Catal. Lett. 2005, 104, 151.
2
In summary, the chiral (salen) Co bearing Lewis acids of
Al and Ga were not only able to activate the enantio-
selective ring opening of terminal epoxide with carb-
oxylic acids, it also catalyze asymmetric cyclization
reaction too. Currently we are looking at the synergistic
effect of Co–Al and Co–Ga on other asymmetric
catalytic reaction for a multifunctional characteristic
of the catalyst.
5. The selectivity factor (k ) was calculated using the equa-
rel
tion = ln[1 À c(1 + ee)]/ln[1 À c(1 À ee)] where ee is the
enantiomeric excess of the ring opened product and c is the
conversion (set to equal the isolated yield).
6
7
8
9
. Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H.-G.;
Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223.
. Nielson, L. P. C.; Stevenson, C. P.; Backmond, D. G.;
Jacobson, E. N. J. Am. Chem. Soc. 2004, 126, 1360.
. Takeichi, T.; Arihara, M.; Ishimori, M.; Tsuruta, T.
Tetrahedron 1980, 36, 3391.
. (a) Brickner, S.; Hutchinson, D.; Barbachyn, M.; Manni-
nen, P.; Ulanowicz, D.; Garmon, S.; Grega, K.; Hendges,
S.; Toops, D.; Ford, C.; Zurenko, G. J. Med. Chem. 1996,
39, 673; (b) Weidner-Wells, M. A.; Boggs, C. M.; Foleno,
B. D.; Melton, J.; Bush, K.; Goldschmidt, R. M.; Hlasta,
D. J. Bioorg. Med. Chem. 2002, 10, 2345.
References and notes
1
2
. H O: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.;
Jacobsen, E. N. Science 1997, 277, 936; Furrow, M. E.;
Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776;