RSC Advances
ARTICLE
5RA0567
DOI: 10.1039Jo/Curnal Na1Cme
spectra were recorded on a Bruker 400 or 500 MHz instrument. 7. M. K. Rosen, R. F. Standaert, A. Galat, M. Nakatsuka and S.
1
H NMR spectra were reported relative to Me Si (δ 0.0 ppm) or
4
L.Schreiber, Science 1990, 248, 863ꢀ866.
1
3
residual CHCl (δ 7.26 ppm). C NMR were reported relative
3
8
.
H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto,
M. Hashimoto and T. Taga, J. Am. Chem. Soc., 1987, 109, 5031ꢀ
to CDCl (δ 77.16 ppm). FTIR spectra were recorded on a
3
Nicolet 6700 spectrometer and were reported in frequency of
ꢀ
1
5
033.b) N. Fusetani, S. Matsunaga, H. Matsumoto and Y.
Takebayashi, J. Am. Chem. Soc., 1990, 112, 7053ꢀ7054.c) C.
Dugave, Curr. Org. Chem., 2002, , 1397ꢀ1431.d) X. J. Wang and F.
A. Etzkorn, Biopolymers, 2006, 84, 125ꢀ146. e) N. Fusetani, S.
Matsunaga, H. Matsumoto and Y. Takebayashi, J. Am. Chem. Soc.
990, 112, 7053ꢀ7054.
absorption (cm ). High resolution mass spectra (HRMS) were
recorded on QꢀTof Micro mass spectrometer.
6
Typical experimental procedure for αꢀ
ketoamides from styrenes
,
1
In a clean reaction tube, I (254 mg, 1.0 mmol) and 9. (a) J. L. Jesuraj and J. Sivaguru, Chem. Commun., 2010, 46, 4791; (b)
2
IBX (280 mg, 1.0 mmol) was taken and dissolved in 2.5 mL of
DMSO by stirring for 5 min at rt followed by addition of
Z. Zhang, Q. Zhang, Z. Ni and Q. Liu, Chem Commun., 2010, 46
,
1
269; (c) K. K. S. Sai, P. M. Esteves, E. Tanoue da Penha and D. A.
styrene (1a, 0.05 mL, 0.5 mmol). The mixture was transferred
o
Klumpp, J. Org. Chem., 2008, 73, 6506; (d) D. Tomita, K.
Yamatsugu, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2009,
131, 6946; (e) L. Yang, D.ꢀX. Wang, Z.ꢀT. Huang and M.ꢀX. Wang,
J. Am. Chem. Soc., 2009, 131, 10390; (g) H. Xu and C. Wolf, Angew.
Chem., Int. Ed., 2011, 50, 12249.
to a 80 C oil bath and stirred for 3.5 hours. Piperidine (1b, 0.2
mL, 2.0 mmol) was added to the stirring solution slowly and
stirred till the reaction was complete. Completion of reaction
was monitored using TLC by checking the complete
disappearance of the intermediate phenylglyoxal (1f). The
reaction was then extracted with ethyl acetate for few times and
the combined organic layer was washed with saturated sodium
thiosulphate and saturated sodium bicarbonate solutions. It was
then dried over anhydrous sodium sulphate, filtered and
1
0. (a) J. Chen and R. F. Cunico, J. Org. Chem., 2004, 69, 5509ꢀ5511.b)
R. Hua, H. Takeda, Y. Abe and M. Tanaka, J. Org. Chem., 2004, 69
,
9
74ꢀ976.
concentrated under reduced pressure. The crude product was 11. F. Ozawa, T. Sugimoto, Y. Yuasa, M. Santra, T. Yamamoto and A.
purified using column chromatography (silicagel, petroleum
ether:ethyl acetate=85:15) to give the desired tertiary αꢀ
Yamamoto, Organometallics, 1984,
C. Zhang, Z. Xu, L. Zhang and N. Jiao, Angew. Chem., Int. Ed., 2011,
, 11088ꢀ11092.
3. C. Zhang, X. Zong, L. Zhang and N. Jiao, Org. Lett., 2012, 14, 3280ꢀ
283.
4. J. Zhang, Y. Wei, S. Lin, F. Liang and P. Liu, Org. Biomol. Chem.
012, 10, 9237ꢀ9242.
5. F.ꢀT. Du and J.ꢀX. Ji, Chem. Sci., 2012,
6. W.ꢀP. Mai, H.ꢀH. Wang, Z.ꢀC. Li, J.ꢀW. Yuan, Y.ꢀM. Xiao, L.ꢀR.
Yang, P. Mao and L.ꢀB. Qu, Chem. Commun. (Cambridge, U. K.)
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3, 683ꢀ692.311.
1
1
1
2
.
3
2
33
34
ketoamide (2a). The data for αꢀketoamides 2a
2kꢀ2m , 2n and 1e are already reported in literature.
ꢀ
2e
, 2fꢀ2i, 2j ,
5
0
3
5
33
36
3
,
Acknowlegment
2
1
1
3, 460ꢀ465.
We thank DST (Project No. SB/S1/OCꢀ72/2013) and DST nano
mission (SR/NM/NSꢀ1034/2012(G) for financial support. KSS
and SD thank for CSIR, New Delhi for research fellowship.
,
2
Notes and references
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Electronic Supplementary Information (ESI) available: R
f
values, IR, 19. A. Y. Shaw, C. R. Denning and C. Hulme, Tetrahedron Lett., 2012,
1
13
NMR and MS data for all the products and copy of H and C spectra
53, 4151ꢀ4153.
for all the compounds are included in the ESI. See. 20. B. Song, S. Wang, C. Sun, H. Deng and B. Xu, Tetrahedron Lett.
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