Viktor Bagutski et al.
FULL PAPERS
to afford sufficiently pure 14a; yield: 3.17 g (93%). An ana-
lytically pure sample was obtained by distillation ofan ali-
quot ofthe crude reaction mixture under reduced pressure,
bp 63–648C/4 mbar.
Supporting Information
1
Full characterization data for all new compounds, and H-
and 13C NMR spectra for 7i, 2j, 10a, and 10d.
Benzyl 2-(BicycloACHTRE[UNG 3.1.0]hex-1-yl)propenoate (15a)
Acknowledgements
To a stirred suspension of finely powdered and flame-dried
K2CO3 (5 g, 36.2 mmol) and KI (3.8 g, 22.9 mmol) in anhy-
drous DMF (40 mL) was added under argon a solution of
the acid 12a (3.3 g, 21.7 mmol) and benzyl chloride (2.9 g,
22.9 mmol) in 10 mL ofthe same solvent in one portion at
ambient temperature. After stirring for an additional 12 h,
the mixture was poured into 250 mL of t-BuOMe and fil-
tered through a short pad ofCelite ꢁ, which was rinsed with
50 mL ofthe same solvent. The ifltrate was washed with
water (2150 mL), brine (100 mL) and dried over anhy-
drous MgSO4. Evaporation ofthe solvents under reduced
pressure gave 5.2 g ofa crude product, which was subjected
to flash chromatography on 100 mL of silica gel, eluting
with pentane to pentane/ether, 20:1, to afford pure 15a
(99.8% pure according to GC); yield: 4.75 g (90%).
This work was supported by the Fonds der Chemischen In-
dustrie and by the European Commission (Contract G5RD-
CT-200100554). The authors thank R. Machinek, C. Zolke,
C. Siebert, U. Leonhardt, M. Weitemeyer, Dr. H. Frauendorf,
G. Udvarnoki and F. Hambloch for analytical support, and
Dr. B. Knieriem for his careful reading of the final manu-
script.
References
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A
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ACHTREUNG
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ꢀ
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ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2006, 348, 2133 – 2147