S. Dai et al. / Tetrahedron 66 (2010) 6919e6923
6923
(
1:4) as eluent. Benzyl alcohols 19 from substrate 15 were isolated
by column chromatography on silica gel with ethyl acetate:
n-hexane (1:1) as eluent. The R value for all alcohols was in the
range of 0.2e0.3. The isolated benzyl alcohols had a purity of >99%
2. Ullmann’s Encyclopaedia of Industrial Chemistry, 6th ed.; Wiley-VCH: Weinheim,
002; Vol. 5; p 83.
2
3
4
. Kim, J. W.; He, J.; Yamaguchi, K.; Mizuno, N. Chem. Lett. 2009, 38, 920e921.
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4390e4393.
f
1
5. Bennur, T. H.; Sabne, S.; Deshpande, S. S.; Srinivas, D.; Sivasanker, S. J. Mol. Catal.
A 2002, 185, 71e80.
(
GC). Their H NMR and Mass (from GCeMS) data were given as
1
1 1
follows: 9 : H NMR (CDCl
3
, 500 MHz):
OH), 2.705e2.750 (m, 2H, CH
d
¼7.221e7.286 (m, 4H, Ph),
6. Das, S.; Bhowmick, T.; Punniyamurthy, T.; Dey, D.; Nath, J.; Chaudhuri, M. K.
4
3
5
2
(
(
.732 (s, 2H, CH
H, CH
), m/z¼136 (M ). Compound 10 : H NMR (CDCl
00 MHz): OH),
¼7.133e7.299 (m, 4H, Ph), 4.679 (s, 2H, CH
.658e2.688 (m, 2H, CH Me), 1.235e1.261 (m, 3H, CH
), m/z¼136
¼7.222e7.383
OH), 2.647e2.678 (m, 2H, CH CH Me),
Me), 0.976e1.005 (m, 3H, CH
), m/z¼150
¼7.111e7.291
OH), 2.586e2.617 (m, 2H, CH CH Me),
), m/z¼150
2
2
Me),1.236e1.266 (m,
Tetrahedron Lett. 2003, 44, 4915e4917.
7. Figiel, P. J.; Sobczak, J. M. New J. Chem. 2007, 31, 1668e1673.
þ
13
1
3
3
,
8
9
. Nishiwaki, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2002, 67, 5663e5668.
. Kiyotak, O. Jpn. Kokai Tokkyo Koho 2,007,186,440, Jul. 2007.
d
2
2
3
10. Du, J.; Chen, Z.; Zou, X. YouJi HuaXue 2004, 24, 1122e1124.
11. Hayes, R.; Li, K. D.; Leeming, P.; Wallace, T. W.; Williams, R. C. Tetrahedron 1999,
þ
14
1
M ). Compound 11 : H NMR (CDCl
m, 4H, Ph), 4.728 (s, 2H, CH
.587e1.688 (m, 2H, CH
3
, 500 MHz): d
5
5, 12907e12928.
2. Wagner, P. J.; Meador, M. A.; Zhou, B.; Park, B. S. J. Am. Chem. Soc. 1991, 113,
9630e9639.
2
2
2
1
1
2
3
þ
27 1
13. Lee, J. P.; Ke, Z.; Ramirez, M. A.; Gunnoe, T. B.; Cundari, T. R.; Boyle, P. D.;
(
(
M ). Compound 12 : H NMR (CDCl
m, 4H, Ph), 4.669 (s, 2H, CH
3
, 500 MHz): d
Petersen, J. L. Organometallics 2009, 28, 1758e1775.
2
2
2
14. Azzena, U.; Demartis, S.; Fiori, M. G.; Melloni, G.; Pisano, L. Tetrahedron Lett.
1
(
(
.621e1.696 (m, 2H, CH
2
Me), 0.938e0.994 (m, 3H, CH
3
1995, 36, 8123e8126.
15. Azzena, U.; Demartis, S.; Melloni, G. J. Org. Chem. 1996, 61, 4913e4919.
þ
28
þ
29
1
M ). Compound 17 : m/z¼156 (M ). Compound 19
:
H NMR
1
1
6. Holland, H. L.; Weber, H. K. Curr. Opin. Biotechnol. 2000, 11, 547e553.
7. Li, Z.; Beilen, J. B.; Duetz, W. A.; Schmid, A.; Raadt, A.; Griengl, H.; Witholt, B.
Curr. Opin. Chem. Biol. 2002, 6, 136e144.
8. Burton, S. G. Trends Biotechnol. 2003, 21, 543e549.
9. Park, J.; Clark, D. S. Biotechnol. Bioeng. 2006, 94, 189e192.
0. Maruyama, T.; Iida, H.; Kakidani, H. J. Mol. Catal. B 2003, 21, 211e219.
CDCl
3
, 500 MHz):
d
¼7.261e7.407 (m, 4H, Ph), 4.708 (s, 2H, CH
2
Cl),
þ
4
.596 (s, 2H, CH
2
OH), m/z¼156 (M ).
1
1
2
Acknowledgements
21. Buehler, B.; Schmid, A.; Hauer, B.; Witholt, B. J. Biol. Chem. 2000, 275,
This work was financially supported by Science and Engineering
Research Council of A*STAR, Singapore, through a research grant
project No. 0621010024).
10085e10092.
2
2. Buehler, B.; Witholt, B.; Hauer, B.; Schmid, A. Appl. Environ. Microbiol. 2002, 68,
560e568.
(
2
2
2
2
3. Nakano, T.; Kawabata, S.; Sugihara, T.; Agatsuma, N.; Kakuda, H.; Mori, Y. Bull.
Chem. Soc. Jpn. 2003, 76, 2353e2360.
4. Nishio, T.; Patel, A.; Wang, Y.; Lau, P. C. K. Appl. Microbiol. Biotechnol. 2001, 55,
Supplementary data
321e325.
5. Liu, L.; Schimid, R. D.; Urlacher, V. B. Appl. Microbiol. Biotechnol. 2006, 72,
876e882.
6. Wang, Z.; Lie, F.; Lim, E.; Li, K.; Li, Z. Adv. Synth. Catal. 2009, 351, 1849e1856.
2
7. Kazuhiko, M.; Masayuki, H.; Keiichiro, N.; Toshio, F. Pestic. Biochem. Physiol.
1
989, 35, 300e314.
References and notes
28. Lindsell, W. D.; Palmer, D. D.; Preston, P. N.; RosairRay, G. M.; Jones, V. H.;
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