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Scheme 5 Coupling of vinyl cyclopropanes with ketones.
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though diastereoselectivity was not achieved (Scheme 5, eqn
(1)). This could have been caused by low E/Z selectivity of the
allylic indiums. The seminal work developed by Buchwald that
was related to a Cu–H catalyzed reaction did not allow the use of
vinyl cyclopropane as a reactant because their method has no
process for a radical opening of the cyclopropane ring (Scheme
5, eqn (2)).9 Our method expands the scope of the dienes by
allowing use of their derivatives.
In summary, we developed a process whereby the reductive
coupling of 1,3-dienes with various ketones could be sufficiently
catalyzed by HInCl2. This approach allowed the introduction of
functional groups into homoallylic alcohols, which generated
sequential Ctert–Ctert bonds with expansion to vinyl cyclopro-
pane 4. Application to an asymmetric version of the coupling
and improvement of the diastereoselectivity are underway.
Conflicts of interest
There are no conicts to declare.
Notes and references
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