Angewandte
Chemie
J = 6.4 Hz, 2H), 5.86 (d, J = 3.2 Hz, 1H), 6.03 (d, J = 3.2 Hz, 1H),
7.27–7.46 ppm (m, 8H); minor diastereoisomer: d = 3.83 (dq, J = 8.8
and 6.4 Hz, 1H), 4.11 ppm (d, J = 8.8 Hz, 1H); 13C{1H} NMR (CDCl3,
100 MHz): major diastereoisomer: d = 13.7, 20.6, 24.2, 44.3, 52.4, 56.3,
78.4, 105.9, 107.5, 125.2, 127.2, 128.1, 128.3, 128.5, 129.7, 140.6, 148.3,
151.2, 153.0 ppm; 77Se{1H} NMR (CDCl3, 76 MHz): major diaster-
eoisomer: d = 236.9 ppm (s); minor diastereoisomer: d = 236.3 ppm
(s). Elemental analysis: calcd for C26H32O3Se: C 66.23, H 6.84; found:
C 66.31, H 6.92.
G. Fragale, T. Wirth, Chem. Eur. J. 2002, 8, 1125; j) M. Tiecco, L.
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[14] An asymmetric intramolecular cyclization of alkenes with
aromatic compounds by using an optically active electrophilic
selenium reagent was reported, but the reaction is not a direct
carboselenenylation; the stepwise reaction first involves an
oxyselenenylation and then a stereoselective intramolecular
cyclization of an episelenonium ion with benzene derivatives to
give the corresponding cyclic products with high diastereoselec-
tivity: R. Dꢁziel, E. Malenfant, C. Thibault, Tetrahedron Lett.
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Received: February 16, 2005
Published online: May 4, 2005
Please note: Minor changes have been made to this manuscript
since its publication in Angewandte Chemie Early View. The Editor.
[15] R. Dꢁziel, S. Goulet, L. Grenier, J. Bordeleau, J. Bernier, J. Org.
Chem. 1993, 58, 3619.
Keywords: alkenes · asymmetric synthesis · diastereoselectivity ·
selenium · synthetic methods
.
[16] The molecular structure of a major diastereoisomer of 5i was
unambiguously clarified by X-ray crystallographic analysis.
CCDC-261554 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
from the Cambridge Crystallographic Data Centre via
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