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2005
Rings with 7 or more members
Q 0050
Metal Carbene Promoted Sequential Transformations for the Enantioselective
of Highly Functionalized Cycloheptadienes. — A highly stereoselective
25- 066 Synthesis
synthesis of functionalized cycloheptadienes is presented, involving the two-step
three-component coupling strategy. This strategy combines an enyne metathesis of
terminal alkynes, e.g. (I), with enol ether (II) to construct alkoxydienes like (III) and
(IV), which undergo a highly stereoselective rhodium-catalyzed [4 + 3] cycloaddition
towards vinyldiazoacetates like (V). The rhodium catalyst does not only differentiate
diene geometry but also causes kinetic resolution in the case of a propargylic stereocenter. — (DENG, L.; GIESSERT, A. J.; GERLITZ, O. O.; DAI, X.; DIVER, S. T.;
DAVIES, H. M. L.; J. Am. Chem. Soc. 127 (2005) 5, 1342-1343; Dep. Chem., Univ.
Buffalo, Amherst, NY 14260, USA; Eng.) — Mischke
2005
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