B. Sun et al. / Tetrahedron: Asymmetry 16 (2005) 1305–1307
1307
(
0
300 MHz, CDCl ): d 0.02 (s, 3H, Me), 0.05 (s, 3H, Me),
Compound 8 (270 mg, 1 mmol), 1 mL of acetic anhy-
dride, 1 mL of pyridine, and 10 mg of DMAP were stir-
red at room temperature for 0.5 h. The reaction mixture
3
.83 (s, 9H, t-Bu), 0.88 (t, J = 6.6 Hz, 3H, Me),1.22 (br s,
2H), 1.38–2.33 (m, 2H), 3.97–3.99 (m, 1H, CHOTBS);
2
1
3
C NMR (75 MHz, CDCl ): d –4.8, –4.6, 14.0, 18.0,
was extracted with Et O and the organic layer washed
2
3
2
2
0.8, 22.6, 24.7, 25.1, 25.5, 25.6, 25.8, 26.3, 29.0, 29.3,
9.5, 31.9, 33.7, 36.0, 39.6, 54.5, 72.2, 218.1; EIMS
with water, brine and dried over anhydrous Na SO .
2
After removal of solvent, the residue was purified by
flash chromatography to afford colorless oil 1 in 100%
4
+
+
+
m/z: 367 (M ꢀ1, 0.1), 353 (M ꢀMe, 109), 311 (M ꢀt-
Bu, 100); HRMS (ESI): calcd for C H O Si+H
2
yield. [a] = ꢀ36.9 (c 1.05, CHCl3); IR (film):
2
44
2
D
+
M +H) 369.3183, found 369.3184.
ꢀ1
1745 cm ; H NMR (300 MHz, CDCl ): d 0.88 (t,
3
1
(
J = 6.8 Hz, 3H, Me), 1.10–1.98 (m, 22H), 2.08 (s, 3H,
CH CO), 2.36–2.64 (m, 2H), 4.32–4.38 (m, 1H,
0
4
.3. (2R)-2-[1 -(S)-Acetoxyundecyl]cyclopentanone 7
3
1
3
CHOAc), 4.94–4.99 (m, 1H, CHOCO); C NMR
A mixture of 254 mg (1 mmol) of 5a, 1 mL of acetic
anhydride, 1 mL of pyridine, and 10 mg of DMAP
was stirred at room temperature for a period of 0.5 h.
(75 MHz, CDCl ): d 14.0, 18.3, 20.9, 22.6, 24.0, 25.3,
3
29.5–29.2 (6 · C), 29.9, 31.8, 73.8, 79.8, 170.7, 171.0;
+
+
EIMS m/z: 312 (M , 1.6), 269 (M ꢀAc, 13), 252
+
+
The reaction mixture extracted with Et O and the
2
(M ꢀAcOH, 32), 99 (M ꢀAcOCHC H , 100);
10 21
+
HRMS (ESI): calcd for C H O +Na (M +Na)
335.2193, found 335.2192.
organic layer washed with water, brine and dried over
anhydrous Na SO . After removal of the solvent, the
1
8
32
4
2
4
residue was purified by flash chromatography (petro-
leum/ethyl acetate = 16:1, v/v) to afford a colorless oil
in 100% yield. [a] = ꢀ42.0 (c 0.80, CHCl ); IR (film):
D
3
Acknowledgements
ꢀ
1 1
1
735, 1256 cm ; H NMR (300 MHz, CDCl ): d 0.82
3
(
CH CO), 1.50–2.30 (m, 2H), 5.16–5.21 (m, 1H,
t, J = 6.6 Hz, 3H, Me), 1.21 (br s, 22H), 1.94 (s, 3H,
This work was financially supported by the National
Natural Science Foundation of China (Grant No
20272020 and 20072012).
3
1
3
CHOAc); C NMR (75 MHz, CDCl ): d 14.1, 20.6,
3
2
2
0.9, 22.6, 24.3, 25.4, 25.5, 25.6, 25.8, 26.3, 29.3, 29.4,
9.5, 31.9, 32.7, 38.7, 51.7, 72.2, 170.1, 218.1; EIMS
+
+
m/z: 296 (M ), 236 (M ꢀOAc, 80); HRMS (ESI): calcd
References
+
for C H O +Na (M +Na) 319.2244, found 319.2250.
1
8
32
3
1
2
. Laurence, B. R.; Pickett, J. A. J. Chem. Soc., Chem.
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4
.4. (5R,6S)-6-Hydroxyhexadecan-5-olide 8
To a solution of 254 mg (1 mmol) of 5a in 15 mL of
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1
mixture was then stirred at room temperature for 4 h,
and extracted with Et O. The organic layer was washed
2
successively with aq NaHCO , water, and brine, and
3
dried. After removal of solvent, the crude product was
purified by flash chromatography (petroleum/ethyl ace-
tate = 2:1, v/v) to afford 220 mg of compound 8 in
8
IR (film): 3440, 2920, 2850 cm ; H NMR (300 MHz,
3. (a) Lin, G. Q.; Xu, H. J.; Wu, B. C.; Guo, G. Z.; Zhou, W.
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2
2
3
.04 g (6 mmol) of m-CPBA was added. The reaction
1
987, 45, 602; (f) Wang, Z. M.; Qian, X. H.; Zhou, W. S.
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D
3
ꢀ
1 1
CDCl ): d 0.87 (t, J = 6.3 Hz, 3H, Me), 1.33 (br s,
1
3
8H, (CH ) ), 1.49–1.94 (m, 4H), 2.42–2.61 (m, 2H),
2 9
4
111; (k) Figadere, B.; Harmange, J. C.; Laurens, A.; Cave,
3
.52–3.58 (m, 1H, CHOH), 4.13–4.18 (m, 1H, CHOCO);
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1
3
A. Tetrahedron Lett. 1991, 32, 57539; (l) van Aar, M. P. M.;
Thijs, L.; Zwanenburg, B. Tetrahedron 1995, 41, 11223; (m)
Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817.
. Peng, L. Z.; Liu, H. W.; Zhang, T.; Zhang, F. Z.; Mei, T.
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3
2
8
4.1, 25.4, 29.3–29.5 (6 · C), 31.8, 32.6, 34.0, 73.3,
+
3.3, 171.7; EIMS m/z: 252 (M ꢀH O, 0.12), 100
2
4
+
(M ꢀOC H , 100); HRMS (ESI): calcd for
C H O +NH (M +NH ) 288.2533, found 288.2538.
1
1
22
+
1
6
30
3
4
4
5. (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am.
Chem. Soc. 2002, 124, 827; (b) List, B.; Lerner, R. A.;
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List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573;
4
.5. (ꢀ)-(5R,6S)-6-Acetoxy-hexadecan-5-olide 1
(
2
d) List, B. Tetrahedron 2002, 58, 5573; (e) List, B. Synlett
001, 11, 1675; (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas,
A mixture of 296 mg (1 mmol) of 7, 504 mg (6 mmol) of
NaHCO , and 1.04 g (6 mmol) of m-CPBA in 15 mL of
3
C. F., III. J. Am. Chem. Soc. 2001, 123, 5260; (g) for
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asymmetric aldol reaction in various contexts, see: Gr o¨ ger,
H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529; (h)
Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Eur. J.
anhydrous CH Cl was stirred at room temperature for
2
2
4
layer was washed successively with aq NaHCO , water,
h. The mixture was extracted with Et O. The organic
2
3
and brine, and dried. After removal of solvent, the crude
product was purified by flash chromatography (petro-
leum/ethyl acetate = 2:1, v/v) to afford 265 mg of title
compound 1 in 85% yield.
2
001, 8, 37; (i) Alcaide, B.; Almendros, P. Eur. J. Org.
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