1
346
T. Murai et al. / Tetrahedron Letters 44 (2003) 1343–1346
4. For recent examples of selenoamides, see: (a) Zhang,
purified by column chromatography on silica gel using
P.-F.; Chen, Z.-C. Synthesis 2000, 1219; (b) Koketsu, M.;
Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66,
hexane–Et O as an eluent to give 0.171 g (70%) of 4a as
a yellow oil.
2
4
099; (c) Koketsu, M.; Takenaka, Y.; Ishihara, H. Syn-
7. Crystal data of 4h: C H NOSe, F =310.30, triclinic,
15
21
W
thesis 2001, 38, 503; (d) Zhang, P.-F.; Chen. Z.-C. J.
Heterocyclic Chem. 2001, 38, 503; (e) Ishihara, H.;
Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc.
space group P2 /c (c14), a=8.804(2), b=13.605(3), c=
1
3
12.211(1)
A
,
,
i=91.74(1)°, V=1461.8(4)
A
,
,
Z=4,
−
3
−1
Dcalcd=1.410 g cm , v (Mo Ka)=25.58 cm , T=296 K,
2
001, 123, 8408; (f) Koketsu, M.; Takenaka, Y.; Hira-
R=0.143, R =0.057, 1271 reflections, GOF=1.00. Crys-
1
matsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181; (g)
Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett.
tallographic Data for 4h have been deposited with the
Cambridge Crystallographic Data Centre as supplemen-
tary publication no. CCDC 197594.
2
001, 42, 5949; (h) Koketsu, M.; Okayama, Y.; Aoki, H.;
Ishihara, H. Heteroatom Chem. 2002, 13, 195; (i) Zhao,
H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32,
8. The signals due to the carbon atom of the CꢁSe group of
anti isomers were observed in higher fields than those of
syn isomers.
3
383.
. (a) Murai, T.; Suzuki, A.; Ezaka, T.; Kato, S. Org. Lett.
000, 2, 311; (b) Murai, T.; Mutoh, Y.; Kato, S. Org.
5
9. As in the reduction of amides, the reaction of
2
selenoamides with LiAlH has been known to give
4
5c
Lett. 2001, 3, 1993; (c) Murai, T.; Suzuki, A.; Kato, S. J.
Chem. Soc., Perkin Trans. 1 2001, 2711; (d) Murai, T.;
Aso, H.; Kato, S. Org. Lett. 2002, 4, 1407 and references
cited therein.
amines.
10. Shimada, K.; Akimoto, S.; Itoh, H.; Nakamura, H.;
Takikawa, Y. Chem. Lett. 1994, 1743.
11. Ogawa, A.; Miyake, J.; Murai, S.; Sonoda, N. Tetra-
6
. Typical experimental procedure for the reaction of a
lithium eneselenolate with a ketone: In a 20-mL two-
necked flask, to a THF solution (2 mL) of LDA (1.2
mmol) was added selenoamide 1a (0.19 g, 1.0 mmol) at
hedron Lett. 1985, 26, 669.
12. As an alternative procedure for the synthesis of b,b-di-
substituted b-hydroxy amides, the addition of
organometallic reagents to b-oxo amides has been
reported. See: (a) Taniguchi, M.; Oshima, K.; Utimoto,
K. Chem. Lett. 1992, 2135; (b) Taniguchi, M.; Fujii, H.;
Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1994, 67,
2514; (c) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massac-
cesi, M.; Rinaldi, S.; Sambri, L. Tetrahedron Lett. 2001,
42, 6093.
0
°C, and the mixture was stirred at 0°C for 10 min under
a nitrogen atmosphere. Acetone (3a) (0.15 mL, 2 mmol)
was then added to the reaction mixture, followed by
water. The reaction mixture was poured onto water and
extracted with Et O (20 mL). The organic layer was dried
2
over MgSO and concentrated in vacuo. The residue was
4